[ CAS No. 122-18-9 ] {[proInfo.proName]}

Name: 122-18-9|N-Benzyl-N,N-dimethylhexadecan-1-aminium chloride|98% (contains <10%H2O)
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SKU: A545178
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Quality Control of [ 122-18-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 122-18-9 ]

Product Details of [ 122-18-9 ]

CAS No. :	122-18-9	MDL No. :	MFCD00011625
Formula :	C₂₅H₄₆ClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SXPWTBGAZSPLHA-UHFFFAOYSA-M
M.W :	396.09	Pubchem ID :	31202
Synonyms :	Benzyldimethylhexadecylammonium chloride	Chemical Name :	N-Benzyl-N,N-dimethylhexadecan-1-aminium chloride

Calculated chemistry of [ 122-18-9 ]

Physicochemical Properties

Num. heavy atoms :	27
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.76
Num. rotatable bonds :	17
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	126.16
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-1.38 cm/s

Lipophilicity

Log Po/w (iLOGP) :	-1.17
Log Po/w (XLOGP3) :	10.33
Log Po/w (WLOGP) :	4.6
Log Po/w (MLOGP) :	2.64
Log Po/w (SILICOS-IT) :	7.82
Consensus Log Po/w :	4.84

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	1.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-7.85
Solubility :	0.00000565 mg/ml ; 0.0000000143 mol/l
Class :	Poorly soluble
Log S (Ali) :	-10.27
Solubility :	0.0000000212 mg/ml ; 0.0000000001 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-10.04
Solubility :	0.0000000359 mg/ml ; 0.0000000001 mol/l
Class :	Insoluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	2.68

Safety of [ 122-18-9 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P273-P280-P305+P351+P338-P310	UN#:	3261
Hazard Statements:	H302+H312-H314-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 122-18-9 ]

* 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.

Upstream synthesis route of [ 122-18-9 ]
Downstream synthetic route of [ 122-18-9 ]

[ 122-18-9 ] Synthesis Path-Upstream 1~5

1
[ 112-69-6 ]
[ 100-44-7 ]
[ 122-18-9 ]

Reference： [1] Yakugaku Zasshi, 1943, vol. 63, p. 589[2] Chem.Abstr., 1951, p. 5100
[3] Patent: US2075958, 1934, ,
[4] Berichte der Bunsengesellschaft/Physical Chemistry Chemical Physics, 1990, vol. 94, # 8, p. 882 - 887
[5] Pharmaceutical Chemistry Journal, 1984, vol. 18, # 11, p. 784 - 787[6] Khimiko-Farmatsevticheskii Zhurnal, 1984, vol. 18, # 11, p. 1344 - 1348
[7] Berichte der Bunsengesellschaft/Physical Chemistry Chemical Physics, 1996, vol. 100, # 7, p. 1147 - 1152
[8] Physical Chemistry Chemical Physics, 1999, vol. 1, # 8, p. 1957 - 1964
[9] Journal of Physical Organic Chemistry, 1999, vol. 12, # 4, p. 325 - 332
[10] Revue Roumaine de Chimie, 2001, vol. 46, # 1, p. 49 - 53
[11] Revue Roumaine de Chimie, 2001, vol. 46, # 1, p. 49 - 53
[12] Antimicrobial Agents and Chemotherapy, 2002, vol. 46, # 5, p. 1469 - 1474
[13] Patent: CN106946716, 2017, A, . Location in patent: Paragraph 0018; 0023
[14] Patent: CN106916071, 2017, A, . Location in patent: Paragraph 0019; 0020; 0023; 0024

2
[ 36653-82-4 ]
[ 122-18-9 ]

Reference： [1] Pharmaceutical Chemistry Journal, 1984, vol. 18, # 11, p. 784 - 787[2] Khimiko-Farmatsevticheskii Zhurnal, 1984, vol. 18, # 11, p. 1344 - 1348

3
[ 100-44-7 ]
[ 30912-93-7 ]
[ 140-11-4 ]
[ 122-18-9 ]

Reference： [1] Journal of the American Chemical Society, 1983, vol. 105, # 6, p. 1567 - 1571

4
[ 4860-03-1 ]
[ 122-18-9 ]

Reference： [1] Pharmaceutical Chemistry Journal, 1984, vol. 18, # 11, p. 784 - 787[2] Khimiko-Farmatsevticheskii Zhurnal, 1984, vol. 18, # 11, p. 1344 - 1348

5
[ 103-83-3 ]
[ 4860-03-1 ]
[ 122-18-9 ]

Reference： [1] Chemische Berichte, 1940, vol. 73, p. 1007

[ 122-18-9 ] Synthesis Path-Downstream 1~19

1
[ 112-69-6 ]
[ 100-44-7 ]
[ 122-18-9 ]

Yield	Reaction Conditions	Operation in experiment
92.1%	In ethanol at 40℃; for 6h; Large scale;	2; 8-9 Example 3 Preparation of Cetyl Dimethylbenzyl Ammonium Chloride Into a 50 L reactor, 6.00 kg (22.3 mol) of cetyldimethylamine, 2.82 kg (22.3 mol) of benzyl chloride and 18.00 kg of ethanol were added, and the mixture was stirred at 40 ° C for 6 h. Then cool down to -5 °C. After the solid is precipitated, it is filtered.Drying gave 8.12 kg of a white solid with a total yield of 92.1%. The purity of cetyldimethylbenzylammonium chloride was 99.4%.
92.1%	In propan-1-ol at 50℃; for 3h; Large scale;	8; 9 Example 8 Preparation of cetyldimethylbenzylammonium chloride 7.00 kg (26.0 mol) was added to a 50 L reactor Cetyldimethylamine,3.36 kg (26.5 mol) of benzyl chloride and 17.50 kg of n-propanol,Stir at 50 ° C for 3 h.Then cool down to -5 °C.After the solids are precipitated,filter,Drying 9.47 kg of white solid,The total yield was 92.1%.The purity of cetyldimethylbenzylammonium chloride was 99.5%.
	at 120℃;

	In acetone for 6h; Heating;
	In water at 60 - 65℃;
	In acetone
	In acetone for 4h; Heating;
	In tetrahydrofuran for 4h; Heating;
	In N,N-dimethyl-formamide at 30℃;
	In N,N-dimethyl-formamide at 40℃; for 2h;
	In butanone Heating;
	In ethyl acetate at 95℃; for 9h;	3 A benzalkonium chloride monomer synthesis process comprising the steps of: (1) Cetyl dimethyl tertiary amine, benzyl chloride and ethyl acetate, respectively, based on the formula, the molar mass ratio of the cetyl dimethyl tertiary amine and benzyl chloride being 1: 1.3; (2) Ethyl acetate into the 300L glass-lined reactor, the cetyl dimethyl tertiary amine and benzyl chloride were thrown into the high slot, open the reactor of the mixing device, at room temperature will be cetyl dimethyl Amine and benzyl chloride in the same proportion into the reactor; (3) Open the heating device, the reactor heated to 95 ° C, incubation reaction 9 hours; (4) Open the circulating cooling water, the product cooled to room temperature, to the crystal completely precipitated; (5) Take out the precipitation of crystals, vacuum suction filtration, filtration process with ethyl acetate 4 times to wash the crystal, leaving the filter cake; (6) In the filter cake by adding ethyl acetate to recrystallize, the crystal at -1.5Mpa, 60 ° C under vacuum conditions to constant weight that high purity pharmaceutical grade benzalkonium chloride monomer.
	With aluminum (III) chloride In glycerol at 50℃; for 8h;	5.1; 5.2; 5.3; 5.4 Example 5 (1) 2 moles of cetyl dimethyl tertiary amine, 1.2 mol of aluminum chloride, 2.1 mol of benzyl chloride and 100 mL of glycerin, respectively,(2) Cetyl dimethyl tertiary and aluminum chloride were dissolved in glycerol in proportion to obtain a mixed system, the mixture was placed in a hydrothermal boiler, the mixture was heated to 50 ° C,(3) To the mixed system of step (2), dropping benzyl chloride was added dropwise at a rate of 40 drops / min, and the mixture was stopped and allowed to stand for 8 hours to obtain a mixture Chloramine monomer;(4) The mixed system of step (3) is filtered and washed three times and recrystallized from glycerol to give benzalkonium chloride.

Reference： [1]Current Patent Assignee: HUBEI GEDIAN HUMANWELL PHARMACEUTICAL EXCIPIENTS CO LTD - CN109553539, 2019, A Location in patent: Paragraph 0035-0036; 0045-0048
[2]Current Patent Assignee: HUBEI GEDIAN HUMANWELL PHARMACEUTICAL EXCIPIENTS CO LTD - CN109553536, 2019, A Location in patent: Paragraph 0047-0050; 0071
[3]Tanaka et al. [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1943, vol. 63, p. 589][Chem.Abstr., 1951, p. 5100] Current Patent Assignee: AKZO NOBEL NV - US2075958, 1934, A
[4]Chinelatto; Fonseca; Kiyan; El Seoud [Berichte der Bunsengesellschaft/Physical Chemistry Chemical Physics, 1990, vol. 94, # 8, p. 882 - 887]
[5]Chernyavskaya, M. A.; Stefanovich, V. V.; Sergeeva, I. A.; Belova, A. S. [Pharmaceutical Chemistry Journal, 1984, vol. 18, # 11, p. 784 - 787][Khimiko-Farmatsevticheskii Zhurnal, 1984, vol. 18, # 11, p. 1344 - 1348]
[6]El Seoud, Omar A.; Okano, Laura T.; Novaki, Luzia P.; Barlow, Graham K. [Berichte der Bunsengesellschaft/Physical Chemistry Chemical Physics, 1996, vol. 100, # 7, p. 1147 - 1152]
[7]Novaki, Luzia P.; El Seoud, Omar A. [Physical Chemistry Chemical Physics, 1999, vol. 1, # 8, p. 1957 - 1964]
[8]Possidonio, Shirley; Siviero, Fabio; El Seoud, Omar A. [Journal of Physical Organic Chemistry, 1999, vol. 12, # 4, p. 325 - 332]
[9]Avram, Ecaterina [Revue Roumaine de Chimie, 2001, vol. 46, # 1, p. 49 - 53]
[10]Avram, Ecaterina [Revue Roumaine de Chimie, 2001, vol. 46, # 1, p. 49 - 53]
[11]Campanac; Pineau; Payard; Baziard-Mouysset; Roques [Antimicrobial Agents and Chemotherapy, 2002, vol. 46, # 5, p. 1469 - 1474]
[12]Current Patent Assignee: Wu Lian - CN106946716, 2017, A Location in patent: Paragraph 0018; 0023
[13]Current Patent Assignee: Wu Lian - CN106916071, 2017, A Location in patent: Paragraph 0019; 0020; 0023; 0024

2
[ 122-18-9 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
89%	In chloroform; water

Reference： [1]Brown, Allan G.; Corbett, David F.; Eglington, A. John; Howarth, T. Trefor [Tetrahedron, 1983, vol. 39, # 15, p. 2551 - 2562]

3
[ 23968-25-4 ]
[ 122-18-9 ]
[ 73901-67-4 ]
[ 87685-39-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In dichloromethane; water	4 N-(1H-pyrazol-1-ylmethyl)-N-(2,4-dimethyl-thien-3-yl)-chloroacetamide (process b) EXAMPLE 4 N-(1H-pyrazol-1-ylmethyl)-N-(2,4-dimethyl-thien-3-yl)-chloroacetamide (process b) To a well stirred mixture of 19.35 g (0.095 mol) of N-(2,4-dimethyl-thien-3-yl)-chloroacetamide, 4.15 g (0.01 mol) of benzyldimethylhexadecyl-ammonium chloride, 40 g (1 mol) of sodium hydroxide, 200 ml of methylene chloride and 40 ml of water are added 17 g (0.11 mol) of solid 1-chloromethyl pyrazolehydrochloride at such a rate, that the temperature does not rise above 25°. When the addition is completed, the reaction mixture is stirred an additional 21/2 hours at ambient temperature. Then 100 ml of water are added. The organic layer is separated, washed with three 200 ml portions of water, dried over Na2 SO4 and evaporated to dryness. The residue is chromatographed on a silica gel column. Elution with hexane-diethylether 1:1 affords the title compound as an analytically pure syrup which crystallized on chilling overnight at -20°, m.p. 88°-89° (recrystallized from diethyl ether).

Reference： [1]Current Patent Assignee: BASF SE - US4666502, 1987, A

4
[ 13755-29-8 ]
[ 122-18-9 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; triethylamine In tetrachloromethane; ethanol; dichloromethane; water; toluene	5 Disodium (5R,6R)-3-(2-acetamido-1-bromoethenylthio)-6-[(1S)-1-sulphonatooxyethyl]-7-oxo-1-azabicyclo[3.2.0.]hept-2-ene-2-carboxylate EXAMPLE 5 Disodium (5R,6R)-3-(2-acetamido-1-bromoethenylthio)-6-[(1S)-1-sulphonatooxyethyl]-7-oxo-1-azabicyclo[3.2.0.]hept-2-ene-2-carboxylate Disodium (5R,6R)-3-[(E)-2-acetamidoethenylthio]-6-[(1S)-1-sulphonatooxyethyl]-7-oxo-1-azabicyclo[3.2.0.]hept-2-ene-2-carboxylate (100 mg) in water (10 ml) was treated with benzyldimethyl-n-hexadecylammonium chloride (180 mg) in dichloromethane (10 ml). After shaking the mixture was separated and the dichloromethane layer was dried (MgSO4) and evaporated in vacuo to leave the diquaternary ammonium salt. This was taken up in dry dichloromethane (5 ml), cooled to -70° (acetone/solid CO2 bath) and a solution of bromine in carbon tetrachloride (0.38 ml 100 mg/ml) was added. The mixture was stirred for 5 min. and then triethylamine (1 eq.) was added. The mixture was warmed to room temperature, diluted with CH2 Cl2 (8 ml) and then washed with water (5 ml). The dichloromethane layer was then extracted with water (2 ml) containing sodium tetrafluoroborate (100 mg) and the resultant aqueous extract was placed on a Biogel P-2 column (83 cm) and eluted with water. Fractions containing 3 to 5 ml of H2 O were collected. Fractions 17-21 showed the expected chromophore. Fractions 22ff showed end absorption, suggesting they contaned inorganic impurities. Fractions 17-21 were combined and evaporated in vacuo to low volume (ca 3 ml) and ethanol (15 ml) was added and evaporated in vacuo to low volume (3), then ethanol was added and evaporated in vacuo to dryness (ZX), then toluene (15 ml) was added to the residue and evaporated in vacuo to leave disodium (5R,6R)-3-(2-acetamido-1-bromoethenylthio)-6-[(1S)-1-sulphonatooxyethyl]-7-oxo-1-azabicyclo[3.2.0.]hept-2-ene-2-carboxylate as a colourless solid, λmax (H2 O) 298 and 250 nm; νmax (KBr) 1750, 1690, 1620 cm-1.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4444783, 1984, A

5
[ CAS Unavailable ]
[ 122-18-9 ]
[ 73521-69-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethyloxonium fluoroborate In dichloromethane; water; ethyl acetate; Petroleum ether	13 Benzyl (5R,6R)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-ethoxysulphonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate STR29 EXAMPLE 13 Benzyl (5R,6R)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-ethoxysulphonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate STR29 Sodium (5R,6R)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-sulphonatooxyethyl]-7-oxo-2-benzyloxycarbonyl-1-azabicyclo[3.2.0]hept-2-ene (e23) (580 mg; containing some inorganic impurities) in water (10 ml) was treated with cetylbenzyldimethylammonium chloride (440 mg) in dichloromethane. After shaking and separating the dichloromethane layer was dried (MgSO4) and evaporated to gvie cetylbenzyldimethylammonium (5R,6R)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-sulphonatooxyethyl]-7-oxo-2-benzyloxycarbonyl-1-azabicyclo[3.2.0]hept-2-ene (e25). This was dissolved in dry dichloromethane (10 ml), cooled to 0° and triethyloxonium tetrafluoroborate under ether (250 mg) and dichloromethane (2 ml) added. The mixture was stirred at 0° for 30 minutes and then at room temperature for 11/2 hours. The solvent was removed by evaporation and the residue chromatographed on silica gel (230-400 mesh ASTM) (6 g) using ethyl acetate as eluant. This failed to effect complete purification so the product was rechromatographed on silica gel (230-400 mesh ASTM) (30 g) eluding with dichloromethane (5 ml), followed by ethyl acetate/petroleum ether (b.p. 60°-80°) mixtures; 1:1 (100 ml), 3:1 (100 ml) and then with neat ethyl acetate. Combination and evaporation of relevant fractions yielded benzyl (5R,6R)-3-[(E)-2-acetamidoethenylthio]-6-[(S)-1-ethoxysulphonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (e24) (153 mg).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4278686, 1981, A

6
[ 122-18-9 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide; bromine; triethylamine; sodium chloride In tetrachloromethane; ethanol; water; toluene; acetonitrile	15 Disodium (5R,6R)-3-(2-Acetamido-1-bromoethenylthio)-6-[(1S)-1-sulphonato-oxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; Isomer I EXAMPLE 15 Disodium (5R,6R)-3-(2-Acetamido-1-bromoethenylthio)-6-[(1S)-1-sulphonato-oxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; Isomer I Disodium (5R,6R)-3-[(E)-2-acetamidoethenylthio]-6-[(1S)-1-sulphonato-oxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.6 g; 80-85% pure) in water (25 ml) was extracted with dichloromethane containing benzyldimethyl-n-hexadecylammonium chloride (1.4 g). The aqueous solution was then re-extracted with dichloromethane containing benzyldimethyl-n-hexadecylammonium chloride (0.2 g). The dichloromethane extract were combined, dried (MgSO4) and the solvent evaporated in vacuo. Toluene (30 ml) was added to the residue and evaporated in vacuo. The residual diquaternary ammonium salt corresponding to the starting material was taken up in dry dichloromethane (40 ml), cooled to -70°, and treated with a solution of bromine in CCl4 (2.2 ml; 100 mg/ml) which had been diluted to 5 ml with dichloromethane. The mixture was stirred at -70° for 3 minutes and triethylamine (160 mg) was added. After stirring at -70° for 15 minutes the mixture was warmed to room temperature, washed with water (10 ml) and extracted with an aqueous solution (15 ml) containing 5% w/v NaCl and sodium iodide (750 mg). The aqueous extract was loaded onto a (previously used) column of DIAION HP20 (particle size 63-75 μm) (3.019.0 cm) and the column was eluted with an aqueous solution containg 5% w/v NaCl (100 ml) followed by deionised water. Fractions were monitored by u.v. and h.p.l.c. Fractions containing u.v. maxima at ca 298 and 246 nm and a peak with a retention time of ca 2.4 min on h.p.l.c. [Waters μ Bondapak C18 Reverse Phase column; elution with pH 4.7 0.05 M NH4 H2 PO4 aqueous solution containing 10% acetonitrile 2 ml/min] were combined and evaporated in vacuo to low volume, ethanol (20 ml) was added and evaporated in vacuo to low volume (3) and then toluene (20 ml) was added and evaporated in vacuo to dryness (3*) to give the first isomer of disodium (5R,6R)-3-(2-acetamido-1-bromoethenylthio)-6-[(1S)-1-sulphonato-oxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (151 mg):λmax (H2 O) 298 (12,700), 246 (15,200) nm; λmax (KBr) 1755, 1690, 1620, 1600(sh) cm-1; δ(D2 O, relative to HOD at 4.63 ppm) 1.51 (3H, d, J 6 Hz), 2.15 (3H, s), 3.06 (1H, dd of ABX J1 18 Hz, J2 9 Hz), 3.46 (1H, dd of ABX, J, 18 Hz, J2 9 Hz), 3.86 (1H, dd, J, 9 Hz, J2 6 Hz), 4.1-4.5 (1H, m), 4.7-5.0 (1H, m), 7.68 (1H, s).
	With sodium iodide; bromine; triethylamine; sodium iodide; sodium chloride In tetrachloromethane; ethanol; water; toluene	16 Disodium (5R,6R)-3-(2-Acetamido-1-bromoethenylthio)-6-[(1S)-1-sulphonato-oxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; Isomer II EXAMPLE 16 Disodium (5R,6R)-3-(2-Acetamido-1-bromoethenylthio)-6-[(1S)-1-sulphonato-oxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate; Isomer II Disodium (5R,6R)-3-[(E)-2-acetamidoethenylthio]-6-[(1S)-1-sulphonato-oxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.2 g; 80-85% pure) in water (50 ml) was extracted with dichloromethane (50 ml) containing benzyldimethyl-n-hexadecylammonium chloride (2.6 g). The aqueous solution was re-extracted with dichloromethane (10 ml) containing benzyldimethyl-n-hexadecylammonium chloride (0.4 g). The dichloromethane extracts were combined, dried (MgSO), and evaporated in vacuo. Toluene (30 ml) was added to the residue and evaporated in vacuo. The residue was taken up in dry dichloromethane (70 ml), cooled to -70° and bromine in CCl4 (4.3 ml; 100 mg/ml) was added. After 5 minutes triethylamine (300 mg) was added and the mixture was allowed to warm to ambient temperature and allowed to stand for 45 minutes. The mixture was extracted with an aqueous solution (15 ml) containing 5% w/v NaCl and NaI(1.5 g) and then re-extracted with an aqueous solution (10 ml) containing 5% w/v NaCl and sodium iodide (0.5 g). The combined extracts were loaded onto a column of (previously used) DIAION HP20 (particle size 63 to 75 μm) (3.019.0 cm) and eluted with an aqueous solution containing 5% w/v NaCl (150 ml), deionised water (400 ml) and then with water containing 10% ethanol. The second isomer was eluted with aqueous ethanol. Fractions containing the second isomer λmax ca 295, 255 nm, h.p.l.c. retention time ca 4.2 min using the system described in EXAMPLE 15) were combined and evaporated in vacuo and the residue was further purified by redissolving in an aqueous solution containing 5% w/v NaCl (7 ml), the pH was adjusted to 7.1 and the resultant solution was loaded onto a column of previously unused DIAION HP 20 (63-75 μm) (3.019.0 cm) and the column eluted with an aqueous solution containing 5% w/v NaCl (20 ml) followed by deionised water. Fractions containing isomer II were combined, the pH adjusted to 7.1 and the solvent evaporated in vacuo to low volume, ethanol (20 ml) was added and evaporated to low volume (3) and then toluene was added and evaporated to dryness (3) to give the second isomer of disodium (5R,6R)-3-(2-acetamido-1-bromoethenylthio)-6-[1S-sulphonatooxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (121 mg):λmax (H2 O) 294 (10,900), 253 (14,200) nm; λmax (KBr) 1755, 1690, 1610 cm-1, δ(D2 O, signals relative to HOD at δ4.56 ppm) 1.41 (3H, d, J 6 Hz), 3.00 (1H, dd of ABX, J1 19 Hz, J2 9.5 Hz) 3.35 (1H, dd of ABX, J1 19 Hz, J2 9 Hz), 3.79 (1H, dd, J1 9 Hz), J2 6 Hz) 4.1-4.5 (1H, m), 4.6-4.9 (1H, m), 7.65 (1H, s).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4444783, 1984, A
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4444783, 1984, A

7
[ CAS Unavailable ]
[ CAS Unavailable ]
[ 122-18-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In 1,4-dioxane; dichloromethane; water	33.ii (ii) (ii) p-Nitrobenzyl 3-[E-2-carbamoylethenylthio]-6-[1-p-nitrobenzyloxycarbonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate STR43 E-2-Carbamoylethenylthioacetate (23 mgs) in dioxan (3 ml) was treated with an aqueous solution of 0.1M sodium hydroxide (3.2 ml). After 15 min. at ambient temperature, the dioxan was removed in vacuo and a further quantity of water (3 ml) was added. This solution was added to a solution of p-nitrobenzyl 3-[pyrimidin-2-ylsulphinyl]-6-[1-p-nitrobenzyloxycarbonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (100 mg) in dichloromethane (6 ml), at 0° C. Cetyldimethylbenzylammonium chloride (1 mg) was added and the mixture vigorously stirred. After ca. 12 hrs t.l.c. analysis (ethyl acetate:ethanol, 9:1) showed reaction had proceeded to completion. The mixture was diluted with dichloromethane and the organic phase separated, dried and solvent removed to give an off-white solid upon trituration with ether. Chromatography on silica gel 60 (Merck Art. 7729; 230-400 ASTM) eluding with ethyl acetate:hexane; 3:1, gave p-nitrobenzyl 3-[E-2-carbamoylethenylthio]6-[1-p-nitrobenzyloxycarbonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (15 mgs; 15%) as a white solid. νmax. (CHCl3), 1790, 1745, 1690(b), 1610, 1590, 1560, 1525 and 1350 cm-1; δ(d6-acetone), 1.45 (3H, d, J 6 Hz; --CH3), 3.48 (1H, dd, J 8, 18 Hz; C4--H), 3.59 (1H, dd, J 10, 18 Hz; C4--H), 3.83 (1H, dd, J 3, 6 Hz; C6--H), 4.45 (1H, m, C5--H), 5.22 (1H, dt, J 7, 14 Hz; C8--H), 5.35 (2H, s, --OCO2 CH2 Ph), 5.55 (2H, ABq, --CO2 CH2 Ph), 6.38 (1H, d, J 17 Hz; =CH.CONH2), 6.46 (1H, broad s, --NH--), 7.00 (1H, broad s, --NH--), 7.65 (1H, d, J 17 Hz; --SCH=), 7.68 and 7.78 (4H, d, J 9 Hz; arom --H), 8.25 and 8.26 (4H, d, J 9 Hz; arom --H).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4477662, 1984, A

8
[ CAS Unavailable ]
[ CAS Unavailable ]
[ 122-18-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In 1,4-dioxane; dichloromethane; water	34 p-Nitrobenzyl 3-[Z-2-carbamoylethenylthio]-6-[1-p-nitrobenzyloxy carbonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate STR44 EXAMPLE 34 p-Nitrobenzyl 3-[Z-2-carbamoylethenylthio]-6-[1-p-nitrobenzyloxy carbonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate STR44 Z-2-Carbamoylethenylthioacetate (23 mgs) in dioxan (3 ml) was treated with an aqueous solution of 0.1M sodium hydroxide (3.2 ml). After 30 mins at ambient temperature the dioxan was removed in vacuo and a further 3 ml of water added. This solution was added to a solution of p-nitrobenzyl-3-[pyrimidin-2-ylsulphinyl]-6-[1-p-nitrobenzyloxycarbonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (100 mg) in dichloromethane (6 ml) at 0° C. Cetyldimethylbenzylammonium chloride (1 mg) was added. After stirring vigorously for 30 mins at 0° C. and ca 12 hrs at ambient temperature, t.l.c. analysis (ethyl acetate) showed completion of reaction. The phases were partitioned and the aqueous phase extracted with dichloromethane. The organic phases were combined, dried and the solvent removed. Chromatography on silica gel 60 (Merck Art. 7729; 230-400 ASTM) eluding with ethyl acetate, gave a yellow solid, which, upon trituration with acetone/ether gave a white solid shown to be p-nitrobenzyl 3-[Z-2-carbamoylethenylthio]-6-[1-p-nitrobenzyloxycarbonyloxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (15 mgs; 15%). νmax. 1795, 1745, 1690(b), 1605, 1590, 1560, 1525 and 1350 cm-1; δ(d6-DMSO) 1.36 (3H, d, J 7 Hz; --CH3), 3.41-3.62 (m, 2CH--H masked by H2 O), 3.89 (1H, dd, J 3, 6 Hz; C6--H), 4.29 (1H, m, C5--H), 5.00 (1H, quint., J 6 Hz; C8--H), 5.33 (2H, s, --OCO2 CH2 Ph), 5.44 (2H, ABq, --CO2 CH2 Ph), 6.58 (1H, d, J 10 Hz; =CHCO--), 7.65 and 7.76 (4H, d, J 9 Hz; arom --H), 7.72 (1H, d, J 10 Hz; --SCH=), 8.24 (4H, d, J 9 Hz; arom--H).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4477662, 1984, A

9
[ 122-18-9 ]
[ CAS Unavailable ]
[ 1349784-88-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	In water at 20℃;

Reference： [1]Location in patent: experimental part Bell, Thomas James; Ikeda, Yasuhisa [Dalton Transactions, 2011, vol. 40, # 39, p. 10125 - 10130]

10
[ 122-18-9 ]
[ CAS Unavailable ]
[ 2159105-03-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	In water at 60℃; for 6h;	Synthesis General procedure: In 250 mL two-necked flask equipped with reflux condenser, thermometer and magnetic stirrer, mandelic acid (1) (7.61 g, 0.05 mol) and water (30 mL) were placed. Next, a solution of potassium hydroxide (2.81 g, 0.05 mol) in 10 mL of water was added. The obtained mixture was heated at 60 °C for 2 h. A solution of alkylbenzyldimethylammonium chloride (3a-j) (0.05 mol) in water was added and the obtained mixture was heated at 60 °C for 6 h. Next, water was distilled off under reduced pressure and content of flask was dried under 60 °C and pressure 1-5 mm Hg. To the dry residue 90 mL of acetone (or methanol) was added and the mixture was cooled for 24 h at about -20 °C. A precipitate of potassium chloride was collected by filtration. A filtrate was concentrated and dried under reduced pressure.

Reference： [1]Wiśniewska, Anna; Lipiński, Piotr F.J.; Woźniak, Krzysztof; Sanjuan-Szklarz, Fabiola W.; Cieniecka-Rosłonkiewicz, Anna; Michalczyk, Alicja; Dabrowski, Zbigniew; Kulig-Adamiak, Anna; Matalińska, Joanna; Leś, Andrzej; Cybulski, Jacek [Acta poloniae pharmaceutica, 2016, vol. 73, # 3, p. 705 - 715]

11
[ 122-18-9 ]
[ 577-11-7 ]
benzyl-n-hexadecyldimethylammonium 1,4-bis(2-ethylhexyl)sulfosuccinate [ No CAS ]

Reference： [1]Physical Chemistry Chemical Physics,2016,vol. 18,p. 15645 - 15653

12
[ 122-18-9 ]
[ 100-00-5 ]
[ 41295-20-9 ]

Yield	Reaction Conditions	Operation in experiment
97.2%	Stage #1: cetyldimethylbenzylammonium chloride; 4-chlorobenzonitrile With dihydrogen peroxide; sodium hydroxide In methanol at 60℃; Large scale; Stage #2: With hydrogen In toluene at 90℃; Autoclave; Large scale;	7 Example 7 1) Etherification:500kg of methanol was added to the reactor and added500kg p-nitrochlorobenzene and 2.5kgHexadecyl dimethyl benzyl ammonium chloride catalyst,Turn on stirring and heat to 60°C,Then, 100 kg of sodium hydroxide solution and 0.2 kg of hydrogen peroxide solution were added dropwise to the reaction, and the reaction was checked by high performance gas chromatography to obtain the etherified product p-nitroanisole.2) will step 1)The etherified product in the cooling down to room temperature, the oil-water phase separation, separation of the organic phase was washed with water, the washed organic phase was distilled under reduced pressure to obtain the etherified oil;3) Catalytic hydrogenation:500 kg of toluene, the etherified oil obtained in step 2), and 10 kg of Raney nickel were added to the autoclave, hydrogen was replaced, and the mixture was heated and stirred. The heating temperature was 90° C. The reaction was checked by high performance gas chromatography until the reaction was completed.4) will step 3)The catalytic hydrogenation reaction system in the cooling reaction to room temperature emulsification occurs, the reaction system is heated to reflux, while hot filtration, the filtered catalyst is recycled, and the filtrate is distilled under reduced pressure to obtain crude p-aminophenyl ether;5) will step 4)The crude product obtained in the distillation yielded p-aminoanisole in a yield of 97.2%, a purity of 99.6%, and a yield of by-product aniline of 0.6%.

Reference： [1]Current Patent Assignee: JIANGSU ZHONGDAN CHEMICAL TECH - CN107915644, 2018, A Location in patent: Paragraph 0039-0050; 0051-0062; 0063-0074; 0075-0086

13
[ CAS Unavailable ]
[ 122-18-9 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
96.1%	at 50℃; for 4.66667h; Inert atmosphere; Reflux;	3 Example 3 Under a nitrogen atmosphere, 1.11 g of NaAlH4 (0.0206 mol) was weighed into a 500 mL three-necked flask.Add 80 mL of tetrahydrofuran, and install a reflux condenser and a constant pressure dropping funnel;Further weigh 10.85 g of cetyldimethylbenzylammonium chloride (0.0274 mol) in a 250 mL flask with an orifice, and then add 80 mL of anhydrous ethylene glycol dimethyl ether.In a 50 ° C oil bath, heated to stir and dissolve; then,Transfer the cetyldimethylbenzylammonium chloride solution to a constant pressure dropping funnel,It was added dropwise to the three-necked bottle within 40 min, and a large amount of white precipitate began to form in the solution;At the end of the dropwise addition, the reaction was further heated to reflux for 4 h; at the end of the reaction, 160 mL of n-heptane was added.Filtration through a sand core funnel to obtain a clear and clear filtrate; the filtrate is then subjected to vacuum distillation.Most of the solvent was removed and finally dried in a 55 ° C oil bath for 2 h under vacuum.Obtaining 10.32 g of a waxy solid,The yield was about 96.1%.

Reference： [1]Current Patent Assignee: SINOCHEM HOLDINGS CORPORATION LTD - CN109280009, 2019, A Location in patent: Paragraph 0032; 0033

14
[ 86290-24-6 ]
[ 89794-02-5 ]
[ 122-18-9 ]
C₂₇H₃₁BCl₃^(1-)*C₂₅H₄₆N⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: 10.0 mmol of the specified boronic ester (I; R1), 30.0 mmol of magnesium turnings and 10.0 mmol of the salt (II) were suspended in a mixture of 3.40 g of anhydrous toluene and 0.73 g of anhydrous tetrahydrofuran in a dry four-neck flask with a mechanical stirrer, thermometer, metal condenser and pressure-equalized dropping funnel under a nitrogen atmosphere, and stirred vigorously for 30 min. The appropriate haloaromatic (III, R4) was added to this solution, at first in undiluted form, until the onset of exothermicity signals the start of the reaction. The remaining total amount of 30.6 mmol of haloaromatic was diluted with 10.0 g of anhydrous toluene and 10.0 g of anhydrous tetrahydrofuran and added dropwise at such a rate that the internal temperature does not exceed 45 C. On completion of addition, the reaction mixture was heated at reflux for 1 h or until the dissolution of the magnesium was complete. The resulting suspension was discharged onto 50 g of ice-water, and the resulting solids are isolated, washed with cold water and dried under reduced pressure. Examples 15, 18, 20 and 27 and 46-52 were extracted from the aqueous phase with 100 ml of ethyl acetate, the solvent was distilled off under reduced pressure and the resulting oils were isolated. The isolated yield for Example 1 that was prepared by this method was 2.87 g (72% of theory), whereas Example 1 prepared according to DE 198 50 139 A1 was obtained in a yield of 47% of theory.The composition of Examples 1-76 and selected physical properties are summarized in Table 2.

Reference： [1]Patent: US2019/276479,2019,A1 .Location in patent: Paragraph 0027; 0107; 0140; 0141

15
[ 122-18-9 ]
[ CAS Unavailable ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol for 2h; Reflux;	2.3 Synthesis of BDHA₂[MCl₄] metallosurfactants General procedure: The benzyldimethylhexadecylammonium based metallosurfactants, BDHA2[MCl4] were synthesized by refluxing 0.050 mol of benzyldimethylhexadecylammonium chloride (BDHAC) with 0.025 mol of anhydrous metal chloride, MCl2 (where M=Mn, Co, Ni, Cu, Zn) in absolute ethanol for 2 h (Scheme S1). The reaction mixtures were left to cool. The solid products were filtered and were recrystallized from methanol, washed several times with small amounts of methanol followed by ether, and dried over fused CaCl2 and stored in vacuum desiccators.