sales@ambeed.com

Structure Search

List Search MOL Search Structure Search

Hello, Sign in

Home Cart 0 Sign in

[ CAS No. 111-58-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Chemical Structure| 111-58-0

Chemical Structure| 111-58-0

Structure of 111-58-0 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 111-58-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 111-58-0 ]

SDS Specification

Alternatived Products of [ 111-58-0 ]

Product Details of [ 111-58-0 ]

CAS No. :	111-58-0	MDL No. :
Formula :	C₂₀H₃₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BOWVQLFMWHZBEF-KTKRTIGZSA-N
M.W :	325.53	Pubchem ID :	5283454
Synonyms :	N-Oleoylethanolamide;Oleamide MEA;NOE;Activity: acid ceramidase inhibitor;N-Oleoylethanolamine;Oleic acid monoethanolamide

Safety of [ 111-58-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 111-58-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 111-58-0 ]

[ 111-58-0 ] Synthesis Path-Downstream 1~36

1
[ 111-58-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With peracetic acid; acetic acid

Reference： [1]Roe; Scanlan; Swern [Journal of the American Chemical Society, 1949, vol. 71, p. 2219]

2
[ 112-80-1 ]
[ 141-43-5 ]
N-oleoylethanolamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96.8%	With Candida antarctica lipase; water In hexane at 65℃; for 3h;	17 Selecting Reaction Systems for the Oleoyl Ethanolamide Synthesis The previous reactions conducted for the synthesis of fatty acid ethanolamide typically result in the formation of undesirable color and odor even though the addition of deodorizers and anti-oxidants has been suggested to improve the product quality (Kolancilar, J. Am. Oil. Chem. Soc. 81:597-98 (2004); Bilyk et al., J. Am. Oil. Chem. Soc. 69:488-91 (1992); Tufvesson et al., Biotechnol. Bioeng. 97:447-53 (2007), which are hereby incorporated by reference in their entirety). In this example, the feasibility of synthesizing oleoyl ethanolamide with a lipase by using an excess ethanolamine as a solvent and hexane as a solvent was compared. Using an excess ethanolamine as a solvent was shown to be effective for the synthesis of fatty acid ethanolamide when triacylglycerol was used as the acyl donor (Kolancilar, J. Am. Oil. Chem. Soc. 81:597-98 (2004); Bilyk et al., J. Am. Oil. Chem. Soc. 69:488-91 (1992), which are hereby incorporated by reference in their entirety).
96%	In dichloromethane at 20℃; for 1h; Cooling with ice;	General Procedure for the Preparation of N-Acylethanolamides (NAEs) General procedure: A solution of fatty acid oleoyl chloride (1.0 mmol) in CH2Cl2 (2 mL) was added dropwise to a solution of ethanolamine (10 mmol) in CH2Cl2 (10 mL) cooled in an ice bath. The reaction mixture was stirred for 1 h at room temperature, then extracted with CHCl3. The organic layer was dried over Na2SO4 and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3 : MeOH=30 : 1) or by recrystallization (AcOEt-hexane) to give N-acylethanolamide.
89%	Stage #1: cis-Octadecenoic acid With 1-[(1-(cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 20℃; for 0.166667h; Inert atmosphere; Stage #2: ethanolamine In dichloromethane; acetonitrile at 20℃; Inert atmosphere;	5 2.3 Synthesis of NAEs (1a-1g) General procedure: These compounds were synthesized according to the procedure described previously with slight modifications (El-Faham and Albericio, 2010) The appropriate acid (0.15 mmol), (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluoro phosphate (COMU, 64.2 mg, 0.15 mmol), and DIPEA (0.05 ml, 0.30 mmol) were dissolved in anhydrous CH2Cl2 (0.5 ml) and CH3CN (2.5 ml) and the resulting orange-red solution was stirred at rt for 10 min under a nitrogen atmosphere. Ethanolamine (3) (0.15 mmol) in CH3CN (0.2 ml) was then injected into the reaction mixture and vigorous stirring at rt was continued until TLC (CH2Cl2/MeOH 98:2) confirmed the completion of the reaction (3-6 h). The reaction mixture was diluted with CH2Cl2 (3 ml) and the resulting mixture was washed with 5% HCl, saturated NaHCO3 and brine. The organic layer was collected, dried over anhydrous Na2SO4, filtered. The solvent was evaporated under reduced pressure and crude purified by flash chromatography.

88%	With Novozym 435, consisting of immobilized Candida antarctica lipase B In hexane at 40℃; for 6h; Enzymatic reaction;
61%	Stage #1: cis-Octadecenoic acid With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In dichloromethane for 1h; Stage #2: ethanolamine In dichloromethane for 2h;
	at 160℃;
29 mg	Stage #1: cis-Octadecenoic acid With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.166667h; Stage #2: ethanolamine With triethylamine In dichloromethane at 20℃; for 0.25h;
	Stage #1: cis-Octadecenoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In ethyl acetate at 20℃; for 1h; Stage #2: ethanolamine In ethyl acetate at 20℃; for 12h;	5.2. Synthesis of fatty acid amides General procedure: All fatty acid amides with different acyl chains and amine heads were synthesized using the same procedure but with different precursor compounds. 2-(1H-Benzotriazole-1-yl)-1,2,3,3-tetramethyluronium tetrafluoroborate (TBTU, 1 equiv) was added to a mixture of compound C1 (1 equiv) and triethylamine (TEA, 2 equiv) in EtOAc. After stirring for 1 h at room temperature, isopropylamine (2 equiv) was added and the reaction mixture was stirred for 12 h. The mixture was washed with water, dried and concentrated to give a residue that was purified by reversed-phase HPLC (YMC ODS-H80) eluting with 80% aqueous CH3CN to yield compound 1 (1.5 mg, 63%);
	Stage #1: cis-Octadecenoic acid With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.0333333h; Stage #2: ethanolamine With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In dichloromethane at 0 - 20℃;	Preparation of Oleoylethanolamide (OEA) Example 1 Preparation of Oleoylethanolamide (OEA) 1 mL DMF, 99.7 mg oleic acid and 80 μL triethylamine were mixed followed by stirring at room temperature for 2 minutes to obtain a mixture. Then, N-ethanolamine (122 μL, 1.0 mmol) and Benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate (BOP) (243.8 mg) were dissolved in CH2Cl2 (1 mL) and then added to the mixture and stirred for 30 minutes under 0° C. to obtain a reaction mixture. The reaction mixture was left to stand at room temperature and then stirred overnight. The reaction mixture was then concentrated under a reduced pressure at 50° C. so as to remove solvent. Subsequently, the resultant residue was purified using silicone column chromatography (n-hexane/EtOAc=1:1) to obtain a compound in a colorless liquid. The purified compound was subjected to high-resolution electron impact mass spectrometry (HREIMS) using a Finnigan TSQ-46C mass spectrometer. The detected experimental data was as follows: calculated value for C20H39O2N [M+1]+; 326.2971. found value: 326.2974. According to the spectrometry data thus detected, the compound was confirmed to be oleoylethanolamide (OEA) having the following chemical structure:
	With zeolite H-beta-22 In hexane at 120℃; for 3h; Inert atmosphere;
	at 90℃; for 1h; Large scale;	1.1 Step 1 282.47kg (1000mol) oleic acid and 61.08kg (1000mol) monoethanolamine were put in the reactor. While stirring, heated to 90°C. After 1 hour of reaction, obtain oleic acid monoethanolamine.

Reference： [1]Current Patent Assignee: IOWA STATE UNIVERSITY OF SCIENCE AND TECHNOLOGY - US2013/303795, 2013, A1 Location in patent: Paragraph 0142; 0143; 0152; 0153
[2]Takao, Koichi; Noguchi, Kaori; Hashimoto, Yosuke; Shirahata, Akira; Sugita, Yoshiaki [Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 4, p. 278 - 285]
[3]Ottria, Roberta; Casati, Silvana; Ciuffreda, Pierangela [Chemistry and Physics of Lipids, 2012, vol. 165, # 7, p. 705 - 711]
[4]Location in patent: experimental part Plastina, Pierluigi; Meijerink, Jocelijn; Vincken, Jean-Paul; Gruppen, Harry; Witkamp, Renger; Gabriele, Bartolo [Letters in Organic Chemistry, 2009, vol. 6, # 6, p. 444 - 447]
[5]Ghidini, Andrea; Scalvini, Laura; Palese, Francesca; Lodola, Alessio; Mor, Marco; Piomelli, Daniele [Journal of Enzyme Inhibition and Medicinal Chemistry, 2021, vol. 36, # 1, p. 1411 - 1423]
[6]Current Patent Assignee: SHELL PLC - US1990453, 1933, A
[7]Roe; Scanlan; Swern [Journal of the American Chemical Society, 1949, vol. 71, p. 2217]
[8]Park, Yoon-Seok; Jang, Hyun-Jung; Lee, Kyung-Ho; Hahn, Tae-Ryong; Paik, Young-Sook [Journal of Agricultural and Food Chemistry, 2006, vol. 54, # 4, p. 1238 - 1242]
[9]Location in patent: experimental part Dang, Hung The; Kang, Gyeoung Jin; Yoo, Eun Sook; Hong, Jongki; Choi, Jae Sue; Kim, Hyung Sik; Chung, Hae Young; Jung, Jee H. [Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 4, p. 1520 - 1527]
[10]Current Patent Assignee: CHINA MEDICAL UNIVERSITY TAIWAN - US2013/172407, 2013, A1 Location in patent: Paragraph 0049
[11]Tkacheva, Anastasia; Dosmagambetova, Inkar; Chapellier, Yann; Mäki-Arvela, Päivi; Hachemi, Imane; Savela, Risto; Leino, Reko; Viegas, Carolina; Kumar, Narendra; Eränen, Kari; Hemming, Jarl; Smeds, Annika; Murzin, Dmitry Yu. [ChemSusChem, 2015, vol. 8, # 16, p. 2670 - 2680]
[12]Current Patent Assignee: SHANGHAI JINZHAO ENERGY SAVING TECHNOLOGY CO LTD - CN103819370, 2016, B Location in patent: Paragraph 0055

3
[ 111-58-0 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; dicyclohexyl-carbodiimide 1) pyridine, 2 w, 2) 20 h; Yield given. Multistep reaction;

Reference： [1]Smrt, Jiri; Hynie, Sixtus [Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 3, p. 927 - 932]

4
[ 112-77-6 ]
[ 141-43-5 ]
[ 111-58-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With triethylamine In dichloromethane at 0 - 20℃; for 4h;	Preparation of N-oleylethanolamine Preparation of N-oleylethanolamine] (0040) 100 mL of dichloromethane (DCM) was added to 5.0 g of ethanolamine (16.62 mmol), and 2.3 mL of triethylamine (16.62 mmol) was added thereto, thereby preparing a reaction solution. A temperature of the reaction solution was decreased to be 0° C. by using an ice bath, and 13.8 mL of oleoyl chloride (CH3(CH2)7CH═CH(CH2)7COCl, 0.1 mol) was slowly added to the reaction solution, followed by stirring at room temperature for 4 hours. After the stirring was completed, 150 mL of water was added, and the resulting solution was extracted with 150 mL of ethyl acetate, and an organic layer was washed with 150 mL of brine. All organic layers were collected and dried over sodium sulfate, and filtered filtrate was subjected to rotary evaporation to remove a solvent. The residue was washed with hexane to obtain 5.27 g of a white solid having a yield of 97%. MS (oleylethanolamine C20H39NO2: 325.53) and NMR results of the obtained solid were as follows. (0041) MS (ESI pos. ion) m/z: 326 (MH+). 1H NMR (600 MHz, CDCl3): 5.92 (br s, 1H), 5.36-5.32 (m, 2H), 3.73 (t, J=5.4 Hz, 2H), 3.42 (q, J=5.4 Hz, 2H), 2.20 (t, J=7.8 Hz, 2H), 2.02-1.99 (m, 4H), 1.66-1.61 (m, 2H), 1.31-1.27 (m, 21H), 0.88 (t, J=7.2 Hz, 3H).
96%	In dichloromethane at 0 - 4℃; for 0.25h;
90%	With pyridine

73%	With triethylamine In dichloromethane at 20℃; Inert atmosphere;
	at 25℃; for 0.25h; Yield given;
	In tetrahydrofuran; N,N-dimethyl-formamide; benzene for 0.25h; Yield given;
	In tetrahydrofuran at 20℃;
2.88 g	With triethylamine In dichloromethane at 20℃; for 0.25h;
	With triethylamine In dichloromethane at -15℃; for 2h; Inert atmosphere;	1.S3; 1.S4; 1.S5; 1.S6; 1.S7 S3: Dissolve 0.05 mL of ethanolamine in 5 mL of methylene chloride, add 0.3 mL of triethylamine, stir in a dry nitrogen atmosphere, obtain an acid chloride solution, and insert a glass rod into the glassware. In the solution, first stir three times clockwise, and then stir three times counterclockwise until there is no precipitation. S4: The resulting acid chloride solution was slowly dropped into the amine mixture, and stirred at a low temperature of -15 °C for 2h; S5: After stirring, the mixture is washed with 10% sodium carbonate solution in 10 mL water, and the aqueous layer is extracted with dichloromethane. The organic layer is washed with saturated brine 10 mL, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain Crude oleoylethanolamine; S6: adding a sufficient amount of saturated aqueous sodium chloride solution to the crude oleoyl ethanolamine prepared, fully shaking and then standing still. The layer is then added to the suspension mixture in a sufficient amount of carbon tetrachloride solution, followed by distillation to remove impurities from the crude oleoylethanolamine; S7: Subsequently, silica gel column chromatography was used to obtain pure oleoyl ethanolamine as a white solid. During the silica gel column chromatography, the column was packed in a dry manner, and the silica gel was loaded into the column through a funnel and beaten with a rubber mallet. The silica gel column allows the silica gel to be filled continuously and evenly, and the middle should not be broken, and a small stream is slowly added into the tube.

Reference： [1]Current Patent Assignee: NEOPHARM CO.,LTD. - US2016/354293, 2016, A1 Location in patent: Paragraph 0039-0041
[2]Astarita, Giuseppe; Di Giacomo, Barbara; Gaetani, Silvana; Oveisi, Fariba; Compton, Timothy R.; Rivara, Silvia; Tarzia, Giorgio; Mor, Marco; Piomelli, Daniele [Journal of Pharmacology and Experimental Therapeutics, 2006, vol. 318, # 2, p. 563 - 570]
[3]Hopper, Darrin W.; Catalano, John G.; Macdonald, Timothy L. [Tetrahedron Letters, 1996, vol. 37, # 44, p. 7871 - 7874]
[4]Coelho, Filipe; Salonen, Laura M.; Silva, Bruno F. B. [New Journal of Chemistry, 2022, vol. 46, # 32, p. 15414 - 15422]
[5]Cravatt, Benjamin F.; Lerner, Richard A.; Boger, Dale L. [Journal of the American Chemical Society, 1996, vol. 118, # 3, p. 580 - 590]
[6]Lin, Sonyuan; Khanolkar, Atmaram D.; Fan, Pusheng; Goutopoulos, Andreas; Qin, Ce; Papahadjis, Demetris; Makriyannis, Alexandras [Journal of Medicinal Chemistry, 1998, vol. 41, # 27, p. 5353 - 5361]
[7]Santos, Webster L.; Heasley, Brian H.; Jarosz, Renata; Carter, Karen M.; Lynch, Kevin R.; Macdonald, Timothy L. [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 13, p. 3473 - 3476] Giuffrida, Andrea; Rodriguez De Fonseca, Fernando; Nava, Felice; Loubet-Lescoulie, Patrick; Piomelli, Daniele [European Journal of Pharmacology, 2000, vol. 408, # 2, p. 161 - 168]
[8]Lynch, Kevin R.; Hopper, Darrin W.; Carlisle, Steven J.; Catalano, John G.; Zhang, Ming; Macdonald, Timothy L. [Molecular Pharmacology, 1997, vol. 52, # 1, p. 75 - 81]
[9]Location in patent: experimental part Morales-Sanfrutos, Julia; Megia-Fernandez, Alicia; Hernandez-Mateo, Fernando; Giron-Gonzalez, Ma Dolores; Salto-Gonzalez, Rafael; Santoyo-Gonzalez, Francisco [Organic and Biomolecular Chemistry, 2011, vol. 9, # 3, p. 851 - 864]
[10]Current Patent Assignee: YANCHENG TEACHERS UNIVERSITY - CN107805210, 2018, A Location in patent: Paragraph 0022-0027; 0031-0035; 0040-0044

5
[ 111-58-0 ]
[ 108549-23-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With 1H-tetrazole

Reference： [1]Hopper, Darrin W.; Catalano, John G.; Macdonald, Timothy L. [Tetrahedron Letters, 1996, vol. 37, # 44, p. 7871 - 7874]

6
[ 111-58-0 ]
[ 34900-26-0 ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: N-oleoylethanolamine With thionyl chloride at 0 - 20℃; for 5.5h; Inert atmosphere; Stage #2: With potassium <i>tert</i>-butylate In toluene at 40℃; for 2h;	4 Preparation of 2-(8-heptadecenyl)-2-oxazoline (OEA-OXA) 3.26 g of N-(2-hydroxyethyl)oleamide are suspended at 0° C. and under nitrogen gas atmosphere in 20 ml of SOCl2. The mixture is stirred at 0° C. for 30 minutes, then at ambient temperature for 5 hours. The solution thus obtained is dry evaporated at a low pressure. The residue is used without further purification. It is suspended in 20 ml of anhydrous toluene and 1.3 g of potassium tert-butoxide are added. The mixture is heated at 40° C. for 2 hours, then it is cooled at 4° C. The solution is extracted 3 times using 6 ml of water and the extracts are disposed. The organic phase is dry evaporated at a low pressure and the brownish residue is purified by distillation under high vacuum at about 0.5 mm Hg. The fraction which distillates at about 180° C. is collected and preserved in inert atmosphere. (Yield: about 88%) The 2-(8-heptadecenyl)-oxazoline product has the following characteristics: Molecular formula C20H37NO; C=78.12%, H=12.13%, N=4.55%, O=5.20%; Solubility: poorly soluble in water, >10 mg/ml in ethanol; Mr 307.5; ESI-MS: 308 (MH+).
48%	With p-toluenesulfonyl fluoride; tetrabutyl ammonium fluoride In tetrahydrofuran for 2h; Heating;

Reference： [1]Current Patent Assignee: EPITECH GROUP SRL - US2015/57269, 2015, A1 Location in patent: Paragraph 0036; 0037
[2]Lin, Sonyuan; Khanolkar, Atmaram D.; Fan, Pusheng; Goutopoulos, Andreas; Qin, Ce; Papahadjis, Demetris; Makriyannis, Alexandras [Journal of Medicinal Chemistry, 1998, vol. 41, # 27, p. 5353 - 5361]

Yield	Reaction Conditions	Operation in experiment
95.1%	Stage #1: With triethylamine; diisopropyl-carbodiimide In dichloromethane at 20℃; for 4h; Stage #2: In ethanol at 20℃; for 0.5h; Inert atmosphere;	2 Preparation of palmitic acid monoethanolamide General procedure: 1) under nitrogen at room temperature,Triethylamine (2 ml) was added dropwise to mercaptomethyl resin (2 g,MATRIX-INN), N-hydroxy maleimide (1.1 g, 9.7 mmol) and DMF (40 ml)In the reaction vessel.After stirring at room temperature for 24 hours,Afterwards, stirring was continued for 4 hours at 55 degrees,After cooling to room temperature and filtered to give NHS resin,Using DMF,Distilled water and isopropyl alcohol were washed twice,NHS resin was obtained after vacuum drying.2) palmitic acid (1.465 g, 5.72 mmol) and the above NHS resin (1.50 g),DIC (diisopropylcarbodiimidediisoprpylcarbodiimide, 0.72 g, 5.72 mmol),Triethylamine (2 ml) was suspended in 15 ml of dichloromethane.The mixture was stirred at room temperature for 4 hours.Then filtered (filtrate retained,Appropriate amount of palmitic acid was detected by HPLC,DIC and solvent,For the next batch of reactions),The collected resin using DMF,Water, isopropanol, and dichloromethane were separately washed twice and dried in vacuo to give 1.70 g of dry resin to obtain an immobilized palmitic acid active ester with a loading of -1.0 mmol / g.3) Ethanolamine (93.2 mg, 1.58 mmol) was added to a flask containing active ester (1.75 g) and 50 ml of BAlcohol suspension,For 0.5 hour,Centrifugal removal of solid resin,The resin was washed twice with ethanol (the resin was left after vacuum drying)The combined liquid phase was concentrated under reduced pressure,453 mg of palmitic monoethanolamide (96.6% yield for ethanolamine) was obtained,Purity> 99.5% (HPLC).
79%
	Oelsaeure, Aethanolamin;

8
[ 141-43-5 ]
[ 120247-04-3 ]
[ 111-58-0 ]

Yield	Reaction Conditions	Operation in experiment
6.5 g	In 1,4-dioxane for 2.5h; Heating;

Reference： [1]Klenova; Belousova [Pharmaceutical Chemistry Journal, 2002, vol. 36, # 8, p. 423 - 424]

9
[ 111-58-0 ]
[ 137348-86-8 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With 1H-tetrazole

Reference： [1]Santos, Webster L.; Heasley, Brian H.; Jarosz, Renata; Carter, Karen M.; Lynch, Kevin R.; Macdonald, Timothy L. [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 13, p. 3473 - 3476]

10
[ 111-58-0 ]
[ 108549-23-1 ]
[ 183323-44-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N-oleoylethanolamine; Dibenzyl N,N-diisopropylphosphoramidite With 1H-tetrazole In dichloromethane for 1h; Stage #2: With dihydrogen peroxide In dichloromethane for 2h;

Reference： [1]Lynch, Kevin R.; Hopper, Darrin W.; Carlisle, Steven J.; Catalano, John G.; Zhang, Ming; Macdonald, Timothy L. [Molecular Pharmacology, 1997, vol. 52, # 1, p. 75 - 81]

11
[ 111-58-0 ]
[ 24435-25-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tetrazole / CH₂Cl₂ / 1 h 1.2: aq. H₂O₂ / CH₂Cl₂ / 2 h 2.1: 50 percent / cyclohexene; Pd/C; acetic acid / tetrahydrofuran / Heating

Reference： [1]Lynch, Kevin R.; Hopper, Darrin W.; Carlisle, Steven J.; Catalano, John G.; Zhang, Ming; Macdonald, Timothy L. [Molecular Pharmacology, 1997, vol. 52, # 1, p. 75 - 81]

12
[ 111-58-0 ]
[ 733017-77-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrazole 2: sulfur / Heating 3: 95 percent / trifluoroacetic acid; triethylsilane / CH₂Cl₂

Reference： [1]Santos, Webster L.; Heasley, Brian H.; Jarosz, Renata; Carter, Karen M.; Lynch, Kevin R.; Macdonald, Timothy L. [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 13, p. 3473 - 3476]

13
[ 111-58-0 ]
[ 733017-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrazole 2: sulfur / Heating

Reference： [1]Santos, Webster L.; Heasley, Brian H.; Jarosz, Renata; Carter, Karen M.; Lynch, Kevin R.; Macdonald, Timothy L. [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 13, p. 3473 - 3476]

14
[ 112-80-1 ]
[ 111-58-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dioxane / 1.5 h / Heating 2: 6.5 g / dioxane / 2.5 h / Heating

Reference： [1]Klenova; Belousova [Pharmaceutical Chemistry Journal, 2002, vol. 36, # 8, p. 423 - 424]

15
[ 112-80-1 ]
[ 111-58-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: oxalyl chloride / dimethylformamide; benzene / 1 h / 0 °C 2: tetrahydrofuran; dimethylformamide; benzene / 0.25 h

Reference： [1]Lin, Sonyuan; Khanolkar, Atmaram D.; Fan, Pusheng; Goutopoulos, Andreas; Qin, Ce; Papahadjis, Demetris; Makriyannis, Alexandras [Journal of Medicinal Chemistry, 1998, vol. 41, # 27, p. 5353 - 5361]

16
[ 111-58-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrazole 2: hydrogen peroxide 3: 100 percent / cyclohexene / 10percent Pd/C

Reference： [1]Hopper, Darrin W.; Catalano, John G.; Macdonald, Timothy L. [Tetrahedron Letters, 1996, vol. 37, # 44, p. 7871 - 7874]

17
[ 111-58-0 ]
[ 183323-44-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrazole 2: hydrogen peroxide

Reference： [1]Hopper, Darrin W.; Catalano, John G.; Macdonald, Timothy L. [Tetrahedron Letters, 1996, vol. 37, # 44, p. 7871 - 7874]

18
[ 112-80-1 ]
[ 111-58-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (COCl)2 / CH₂Cl₂ / 4 h / 25 °C 2: 0.25 h / 25 °C

Reference： [1]Cravatt, Benjamin F.; Lerner, Richard A.; Boger, Dale L. [Journal of the American Chemical Society, 1996, vol. 118, # 3, p. 580 - 590]

19
[ 111-58-0 ]
[ 541-41-3 ]
[ 318959-79-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 4-methyl-morpholine In tetrahydrofuran at 4 - 20℃; for 24.5h;	13 3.3 g of N-(2-hydroxyethyl) oleoylamide (10 mmoles) was dissolved in 75 ml of tetrahydrofuran (THF) with stirring. The solution was cooled to 4° C. and supplemented with 1.11 g of N-methyl morpholine (11 mmoles) and 1.19 g of ethyl chloroformate (11 mmoles). The resulting mixture was kept at 4° C. for 30 minutes with continuous stirring and then for a further 24 hours at ambient temperature. The mixture was then evaporated to dryness under vacuum. The residue was taken up with 50 ml of water and extracted 3 times with 30 ml of ethyl acetate; the organic phases were washed twice with 20 ml of water, recombined and evaporated to dryness. The residue was purified by preparative chromatography on silica gel with the use of a mixture of ethyl acetate and hexane in a ratio of 50:50, as the eluent. The fractions containing the product were recombined and evaporated to dryness. The oily residue was dried under a high degree of vacuum (yield 80%).The product, N-[2-(ethoxycarbonyl)oxyethyl]oleoylamide had the following chemical and physical characteristics: empirical formula: C23H43NO4 formula weight: 397.40 elemental composition: C = 69.48%; H = 10.90%; N = 3.52%; O = 16.10% solubility in water: slightly soluble solubility in 10 mg/ml in ethanol, organic solvents: ethyl acetate and n-octanol TLC in 100% ethyl acetate: Rf = 0.63 TLC in heptane/isopropanol/ethyl acetate/water (40:20:50:2): Rf = 0.69

Reference： [1]Current Patent Assignee: INNOVET ITALIA - US6864285, 2005, B1 Location in patent: Page column 15; 16

20
[ 135422-90-1 ]
[ 111-58-0 ]
[ 135391-78-5 ]

Yield	Reaction Conditions	Operation in experiment
90%		44 Preparation of 2-(N-Oleoylamino)ethyl 3-[N-(2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl)amino]propionate EXAMPLE 44 Preparation of 2-(N-Oleoylamino)ethyl 3-[N-(2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl)amino]propionate N-(2-Hydroxyethyl)oleamide (0.97 g) and 0.78 g of 3-[N-(2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl)amino]propionic acid were reacted in the same manner as in Example 15 to obtain 1.50 g of the title compound (yield: 90%). property: Oily, IR(cm-1, neat): νC=O 1742, 1658. Mass Spectrometric Analysis: Molecular Formula: C32 H58 N2 O6, Calculated: 566.4254, Found: 566.4274. NMR(δ, CDCl3): 0.88 (3H,t,J=7Hz), 0.98 (3H,s), 1.03 (3H,s), 1.22-1.38 (18H,m), 1.43 (3H,s), 1.47 (3H,s), 1.50-1.72 (5H,m), 1.92-2.08 (4H,m), 2.21 (2H,t,J=7Hz), 2.56 (2H,t,J=6Hz), 3.29 (1H,d,J=12Hz), 3.42-3.70 (4H,m), 3.66 (1H,d,J=12Hz), 4.08 (1H,s), 4.18 (1H,s), 5.28-5.40 (2H,m), 6.27-6.38 (1H,brs), 6.88-6.96 (1H,brs),
90%		44 Preparation of 2-(N-Oleoylamino)ethyl 3-[N-(2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl)amino]propionate Example 44 Preparation of 2-(N-Oleoylamino)ethyl 3-[N-(2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl)amino]propionate N-(2-Hydroxyethyl)oleamide (0.97 g) and 0.78 g of 3-[N-(2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl)amino]propionic acid were reacted in the same manner as in Example 15 to obtain 1.50 g of the title compound (yield: 90%). property: Oily IR(cmmin1, neat): νC=O1742, 1658 Mass Spectrometric Analysis: Molecular Formula: C32H58N2O6 Calculated: 566.4254 Found: 566.4274 NMR(δ, CDCl3): 0.88 (3H,t,J=7Hz), 0.98 (3H,s), 1.03 (3H,s), 1.22-1.38 (18H,m), 1.43 (3H,s), 1.47 (3H,s), 1.50-1.72 (5H,m), 1.92-2.08 (4H,m), 2.21 (2H,t,J=7Hz), 2.56 (2H,t,J=6Hz), 3.29 (1H,d,J= 12Hz), 3.42-3.70 (4H,m), 3.66 (1H,d,J=12Hz), 4.08 (1H,s), 4.18 (1H,s), 5.28-5.40 (2H,m), 6.27-6.38 (1H,brs), 6.88 6.96 (1H,brs)

Reference： [1]Current Patent Assignee: H.U. GROUP HOLDINGS, INC. - US5120738, 1992, A
[2]Current Patent Assignee: H.U. GROUP HOLDINGS, INC. - EP421441, 1991, A2

21
[ 111-58-0 ]
[ 813-77-4 ]
[ 213738-79-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With 1-methyl-1H-imidazole In dichloromethane for 40h;	1 Dimethyl 2-amino-2-N-oleoyl-ethylphopshate (Compound 59) To a mixture of amide Compound 51 (1.0 g, 3.1 mmol) and dimethyl chlorophosphate (0.50 mL, 4.6 mmol) in dry CH2Cl2 (100 mL) under N2 was added N-methylimidazole (0.73 mL, 9.2 mmol). After 40 hours, TLC analysis showed the reaction to be completed and the mixture was washed with sat. NaHCO3 (3×20 mL) , dried (MgSO4) and evaporated to dryness to give dimethyl phosphate Compound 59 (1.2 g, 89%) as a pale yellow oil.1H NMR (360 MHz; CDCl3): (0.75 (3 H, t, J 6.5 Hz, Me), 1.16 (20 H, apparent br d, separation 11.5 Hz, -(CH2)4- and -(CH2)6-), 1.50 (2 H, br s, (-H2), 1.88 (4 H, apparent br d, separation 5.5 Hz, -CH2CHCHCH2-), 2.08 (2 H, t, J 7.5 Hz, (-H2), 3.34-3.38 (2 H, m, 2-H2), 3.64 and 3.67 (each 3 H, s, 2×OMe), 3.97-4.02 (2 H, m, 1-H2), 5.16-5.26 (2 H, m, -CH2CHCHCH2-) and 6.79 (1 H, br s, N-H); 31P NMR (146 Mhz; CDCl3): (2.49; ESI-MS (m/z, +ve): 434 (MH+, 100%).

Reference： [1]Current Patent Assignee: EVOTEC AG; LXR BIOTECHNOLOGY INC; SKY HIGH LLC - US6949528, 2005, B1 Location in patent: Page/Page column 47

22
[ 111-58-0 ]
[ 1309161-76-9 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorine; iron In dichloromethane at 0℃;

Reference： [1]Location in patent: experimental part Skonberg, Christian; Artmann, Andreas; Cornett, Claus; Hansen, Steen Honore; Hansen, Harald S. [Journal of Lipid Research, 2010, vol. 51, # 10, p. 3062 - 3073]

23
[ 77-77-0 ]
[ 111-58-0 ]
[ 1226976-06-2 ]

Yield	Reaction Conditions	Operation in experiment
51%	With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.333333h;

Reference： [1]Location in patent: experimental part Morales-Sanfrutos, Julia; Megia-Fernandez, Alicia; Hernandez-Mateo, Fernando; Giron-Gonzalez, Ma Dolores; Salto-Gonzalez, Rafael; Santoyo-Gonzalez, Francisco [Organic and Biomolecular Chemistry, 2011, vol. 9, # 3, p. 851 - 864]

24
[ 112-80-1 ]
[ 111-58-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / 1 h / 20 °C 2: triethylamine / dichloromethane / 0.25 h / 20 °C
	Multi-step reaction with 2 steps 1: sulfuric acid 2: acetonitrile / 24 h
	Multi-step reaction with 2 steps 1: sulfuric acid / 4 h / 65 °C 2: acetonitrile / 24 h / 130 °C

Reference： [1]Morales-Sanfrutos, Julia; Megia-Fernandez, Alicia; Hernandez-Mateo, Fernando; Giron-Gonzalez, Ma Dolores; Salto-Gonzalez, Rafael; Santoyo-Gonzalez, Francisco [Organic and Biomolecular Chemistry, 2011, vol. 9, # 3, p. 851 - 864]
[2]Dos Santos, Daiane S.; Piovesan, Luciana A.; D'Oca, Caroline R. Montes; Hack, Carolina R. Lopes; Treptow, Tamara G.M.; Rodrigues, Marieli O.; Vendramini-Costa, Débora B.; Ruiz, Ana Lucia T.G.; De Carvalho, João Ernesto; D'Oca, Marcelo G. Montes [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 2, p. 340 - 347]
[3]Antiqueira-Santos, Priscila; dos Santos, Daiane S.; Hack, Carolina R. L.; Flores, Alex Fabiani C.; Montes D’Oca, Marcelo G.; Piovesan, Luciana A.; Nery, Luiz Eduardo M.; Votto, Ana Paula S. [Medicinal Chemistry Research, 2017, vol. 26, # 11, p. 2727 - 2736]

25
[ 111-58-0 ]
[ 1415264-52-6 ]

Yield	Reaction Conditions	Operation in experiment
	With trifluoroacetic acid In chloroform-d1 for 72h;

Reference： [1]Ottria, Roberta; Casati, Silvana; Ciuffreda, Pierangela [Chemistry and Physics of Lipids, 2012, vol. 165, # 7, p. 705 - 711]

26
[ 1415264-52-6 ]
[ 111-58-0 ]

Yield	Reaction Conditions	Operation in experiment
	With perdeuteriopyridine for 24h;

Reference： [1]Ottria, Roberta; Casati, Silvana; Ciuffreda, Pierangela [Chemistry and Physics of Lipids, 2012, vol. 165, # 7, p. 705 - 711]

27
[ 111-58-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride at 0 - 20℃; for 5.5h; Inert atmosphere;	4 Preparation of 2-(8-heptadecenyl)-2-oxazoline (OEA-OXA) 3.26 g of N- (2-hydroxyethyl) oleamide are suspended at 0°C and under nitrogen gas atmosphere in 20 ml of S0C12. The mixture is stirred at 0°C for 30 minutes, then at ambient temperature for 5 hours. The solution thus obtained is dry evaporated at a low pressure. The residue is used without further purification. It is suspended in 20 ml of anhydrous toluene and 1.3 g of potassium tert- butoxide are added. The mixture is heated at 40°C for 2 hours, then it is cooled at 4°C. The solution is extracted 3 times using 6 ml of water and the extracts are disposed. The organic phase is dry evaporated at a low pressure and the brownish residue is purified by distillation under high vacuum at about 0.5 mm Hg. The fraction which distillates at about 180°C is collected and preserved in inert atmosphere. (Yield: about 88%) The 2- ( 8-heptadecenyl ) -oxazoline ' product has the following' characteristics: Molecular formula C20H37NO; C=78.12%, H=12.13%, N=4.55%, 0=5.20%; Solubility: poorly soluble in water, >10mg/ml in ethanol; Mr 307.5; ESI-MS: 308 (MH+) .

Reference： [1]Current Patent Assignee: EPITECH GROUP SRL - WO2013/121449, 2013, A1 Location in patent: Page/Page column 14; 15

28
[ 111-58-0 ]
[ 6301-24-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride / 5.5 h / 0 - 20 °C / Inert atmosphere 2: potassium <i>tert</i>-butylate / toluene / 2 h / 40 °C

Reference： [1]Current Patent Assignee: EPITECH GROUP SRL - WO2013/121449, 2013, A1

29
[ 108-55-4 ]
[ 111-58-0 ]
[ 1613511-80-0 ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide at 20℃; for 1h;	5 g oleoylethanolamide (OEA) (3.07 mmol) was reacted with 0.53 g of glutaric anhydride (4.5 mmol) in 10 mlof dry dimethylformamide. The mixture was kept under stirring at room temperature for 1h. Then 3 ml of HCl 2N and 20ml of cold water were added and the mixture was extracted 3 times with 10 ml chloroform. Organic phases were collected,dried over anhydrous MgSO4 and evaporated in vacuum. The crude product was purified by chromatography on a silicagel column using a mixture 9.8/0.2 chloroform/methanol as eluent. The product was finally crystallized from chloroform/hexane 1:1. 1HNMR (CDCl3): d 0.88 (t, 3H), 1.27-1.33 (m,8H), 1.35 (m, 2H), 1.63 (m, 2H), 1.92 (m,2H), 2.01 (dd,4H),2.31 (t, 2H), 2.40-2.45 (m, 4H), 5.37 (m, 2H), 4.22 (t, 2H), 4.29 (t, 3H) Mass (m/z): M+=440.5 (425)

Reference： [1]Current Patent Assignee: EPITECH GROUP SRL - EP2742957, 2014, A1 Location in patent: Paragraph 0028

30
[ 112-62-9 ]
[ 141-43-5 ]
N-oleoylethanolamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile for 24h;	Synthesis General procedure: Amides 4-7 were synthesized from fatty acid methyl esters (FAMEs) obtained via esterification of the respective fatty acid. The aminolysis reaction of FAMEs (0.3mmol) was realized in the presence of the amines (1.8mmol) and acetonitrile for 24h. The progress of the reactions was monitored by silica gel TLC. The raw products were purified via column chromatography on silica gel (n-hexane/ethyl acetate, 7:3) and analyzed by proton and carbon NMR IR, and ESI-MS/MS. The presented spectroscopic data are in agreement with the literature
	With sodium methylate In methanol at 35℃; for 2h;	3 In the reaction kettle adding 1mmol oleic acid methyl ester and 10mmol mono-ethanolamine, adding the substrate of reaction mass percentage of 0.5% methanol solution of sodium methoxide (30% wt) as catalyst, in the 35 °C, 500 rpm conditions following reaction 2h. For 5% HCl acid removing reaction of the crude product in excess of monoethanolamine, washing to remove residual acid. The use of mixed solvent (hexane: isopropanol=1:1, v/v) the reaction product dissolved and diluted to a suitable concentration, by HPLC-ELSD analysis, oleic acid monoethanolamide content is 98.67%.
	In acetonitrile at 130℃; for 24h;

Reference： [1]Dos Santos, Daiane S.; Piovesan, Luciana A.; D'Oca, Caroline R. Montes; Hack, Carolina R. Lopes; Treptow, Tamara G.M.; Rodrigues, Marieli O.; Vendramini-Costa, Débora B.; Ruiz, Ana Lucia T.G.; De Carvalho, João Ernesto; D'Oca, Marcelo G. Montes [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 2, p. 340 - 347]
[2]Current Patent Assignee: JIANGNAN UNIVERSITY - CN106242988, 2016, A Location in patent: Paragraph 0033; 0034
[3]Antiqueira-Santos, Priscila; dos Santos, Daiane S.; Hack, Carolina R. L.; Flores, Alex Fabiani C.; Montes D’Oca, Marcelo G.; Piovesan, Luciana A.; Nery, Luiz Eduardo M.; Votto, Ana Paula S. [Medicinal Chemistry Research, 2017, vol. 26, # 11, p. 2727 - 2736]

31
[ 112-80-1 ]
[ 141-43-5 ]
[ 111-58-0 ]
[ 1352632-10-0 ]

Yield	Reaction Conditions	Operation in experiment
	In hexane at 180℃; for 3h; Inert atmosphere;

Reference： [1]Tkacheva, Anastasia; Dosmagambetova, Inkar; Chapellier, Yann; Mäki-Arvela, Päivi; Hachemi, Imane; Savela, Risto; Leino, Reko; Viegas, Carolina; Kumar, Narendra; Eränen, Kari; Hemming, Jarl; Smeds, Annika; Murzin, Dmitry Yu. [ChemSusChem, 2015, vol. 8, # 16, p. 2670 - 2680]

32
[ 112-80-1 ]
[ 60-33-3 ]
[ 141-43-5 ]
[ 111-58-0 ]
[ 68171-52-8 ]

Yield	Reaction Conditions	Operation in experiment
70.3%	With sodium methylate In ethanol; hexane for 3h;	Optimization of oleoyl ethanolamide synthesis The optimization reactions were conducted with 1.77 gHOSO (2 mmol) and 1.22 g ethanolamine (20 mmol) andmagnetic stirring (250 rpm). For the initial study of solventsystems, 1 % (relative to the weight of the reactants) sodiummethoxide was used and the reaction was allowed to proceedfor 3 h. The reaction was performed in 1 mL of one of a varietyof solvents or in a solvent-free system. The selected solventsincluded hexane, ethanol, hexane/ethanol 1:1 (v/v), andacetone. At the end of the reaction, the solvents were removedby evaporation at reduced pressure. The crude reaction productwas diluted to 1 mg/mL with hexane and subsequentlyquantified by HPLC. All crude products obtained from theoptimization experiments were treated with the same process.To study the effect of system dilution, the total solventvolume was then varied between 0.5 and 2.0 mL. Next,the amount of catalyst was varied between 1.0 and 2.5 %.Finally, the reaction time was then studied on an hourlybasis.

Reference： [1]Wang, Xiaosan; Han, Zhengyang; Chen, Yang; Jin, Qingzhe; Wang, Xingguo [Journal of the American Oil Chemists' Society, 2016, vol. 93, # 1, p. 125 - 131]

33
[ 111-58-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: cation exchange resin / 4 h / 200 °C / Inert atmosphere; Large scale 2: potassium bisulfite / water / Large scale

Reference： [1]Current Patent Assignee: SHANGHAI JINZHAO ENERGY SAVING TECHNOLOGY CO LTD - CN103819370, 2016, B

34
[ 111-58-0 ]
[ 110-16-7 ]
[ 1612825-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With cation exchange resin at 200℃; for 4h; Inert atmosphere; Large scale;	1.2 Step 2 The oleic acid monoethanolamine produced in the step 1 reaction and 58.04 kg (500 mol) of maleic acid were added to the reaction vessel. 8 kg of cation exchange resin was added. Charged with nitrogen to convert the atmosphere within the reactor to react. Reaction temperature: 200°C; Reaction time: 4 hours; After the reaction, the water was discharged under reduced pressure. Removing the cation exchange resin, obtained oleic acid monoethanolamine maleate.

Reference： [1]Current Patent Assignee: SHANGHAI JINZHAO ENERGY SAVING TECHNOLOGY CO LTD - CN103819370, 2016, B Location in patent: Paragraph 0056

35
N-oleoylethanolamine [ No CAS ]
[ 2601-90-3 ]

Yield	Reaction Conditions	Operation in experiment
98.4%	With sodium hypochlorite; 4-methoxy-2,2,6,6-tetramethylpiperidin-1-oxyl radical; sodium chloride; sodium hydroxide In cyclohexane for 2h; Industrial scale; Green chemistry;	3 Example 3: 1.5 g of oleic acid monoethanolamide (OMEA), 31 ml of cyclohexane and 60 mg of 4-methoxy-2,2,6,6-tetramethylpiperidine-1-oxyl catalyst were mixed and stirred. 21.5 mg of NaCl was dissolved in 6 ml of water, and 38 ml of water was added11.5% aqueous solution of NaClO and 2.3 ml of 2 mol of NaOH aqueous solution. Mix the aqueous solution slowlyWas added dropwise to the organic system of OMEA and catalyst, and the whole process was continued for 2 hours. System appears pointsLayer, and the lower layer of the water-rich phase at pH 3 was 12.8. Cryogenic cooling cycle cooling, the system temperatureGt; 40 C. & lt; / RTI & gt; After completion of the dropwise addition, the reaction was stirred for 2 hours. At the end of the reaction the pH was 7.9. ToneThe pH was then separated, the lower aqueous phase was extracted with cyclohexane, and the cyclohexane layer was combined with rotary evaporation to remove the solvent.And dried in vacuo to give oleoylglycine in a yield of 98.4%.

Reference： [1]Current Patent Assignee: JIANGNAN UNIVERSITY - CN105503637, 2016, A Location in patent: Paragraph 0031; 0032

36
[ 111-58-0 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
96%	With toluene-4-sulfonic acid In benzene for 20h; Reflux; Dean-Stark;

Reference： [1]Coelho, Filipe; Salonen, Laura M.; Silva, Bruno F. B. [New Journal of Chemistry, 2022, vol. 46, # 32, p. 15414 - 15422]

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 111-58-0 ]

Alkenes

[ 1094209-17-2 ]

(Z)-N-(2-Hydroxyethyl)heptadec-10-enamide

Similarity: 1.00

[ 94421-67-7 ]

(Z)-N-(2-Hydroxyethyl)hexadec-9-enamide

Similarity: 1.00

[ 5839-65-6 ]

N-(2-((2-Hydroxyethyl)amino)ethyl)oleamide

Similarity: 0.94

[ 94109-06-5 ]

(Z)-N-(2-Hydroxypropyl)docos-13-enamide

Similarity: 0.94

Aliphatic Chain Hydrocarbons

[ 1094209-17-2 ]

(Z)-N-(2-Hydroxyethyl)heptadec-10-enamide

Similarity: 1.00

[ 94421-67-7 ]

(Z)-N-(2-Hydroxyethyl)hexadec-9-enamide

Similarity: 1.00

[ 5839-65-6 ]

N-(2-((2-Hydroxyethyl)amino)ethyl)oleamide

Similarity: 0.94

[ 94109-06-5 ]

(Z)-N-(2-Hydroxypropyl)docos-13-enamide

Similarity: 0.94

Alcohols

[ 1094209-17-2 ]

(Z)-N-(2-Hydroxyethyl)heptadec-10-enamide

Similarity: 1.00

[ 94421-67-7 ]

(Z)-N-(2-Hydroxyethyl)hexadec-9-enamide

Similarity: 1.00

[ 5839-65-6 ]

N-(2-((2-Hydroxyethyl)amino)ethyl)oleamide

Similarity: 0.94

[ 94109-06-5 ]

(Z)-N-(2-Hydroxypropyl)docos-13-enamide

Similarity: 0.94

Amides

[ 1094209-17-2 ]

(Z)-N-(2-Hydroxyethyl)heptadec-10-enamide

Similarity: 1.00

[ 94421-67-7 ]

(Z)-N-(2-Hydroxyethyl)hexadec-9-enamide

Similarity: 1.00

[ 5839-65-6 ]

N-(2-((2-Hydroxyethyl)amino)ethyl)oleamide

Similarity: 0.94

[ 94109-06-5 ]

(Z)-N-(2-Hydroxypropyl)docos-13-enamide

Similarity: 0.94

Amines

[ 1094209-17-2 ]

(Z)-N-(2-Hydroxyethyl)heptadec-10-enamide

Similarity: 1.00

[ 94421-67-7 ]

(Z)-N-(2-Hydroxyethyl)hexadec-9-enamide

Similarity: 1.00

[ 5839-65-6 ]

N-(2-((2-Hydroxyethyl)amino)ethyl)oleamide

Similarity: 0.94

[ 94109-06-5 ]

(Z)-N-(2-Hydroxypropyl)docos-13-enamide

Similarity: 0.94

Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere