2-Carboethoxyimidazole | Esters

2-Carboethoxyimidazole is an organic compound with catalytic and synthetic activity, used as an intermediate in drug synthesis and functioning by regulating chemical reactions.

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Quality Control of 2-Carboethoxyimidazole Purity: 98% SDS Specification

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NMR

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Product Details of 2-Carboethoxyimidazole

CAS No. :	33543-78-1
Formula :	C₆H₈N₂O₂
M.W :	140.14
SMILES Code :	C1=C[NH]C(=N1)C(OCC)=O
MDL No. :	MFCD03426031
InChI Key :	UHYNYIGCGVDBTC-UHFFFAOYSA-N
Pubchem ID :	549404

Safety of 2-Carboethoxyimidazole

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Application In Synthesis of 2-Carboethoxyimidazole

* 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 [ 33543-78-1 ]

[ 33543-78-1 ] Synthesis Path-Downstream 1~35

1
[ 33543-78-1 ]
[ 16042-25-4 ]

Yield	Reaction Conditions	Operation in experiment
	With water; lithium hydroxide; In tetrahydrofuran; for 1.5h;Reflux;	PREPARATION 321 W-lmidazole-2-carboxylic acid 21.75 mL (43.5 mmol) of a 2M solution of lithium hydroxide in water were added to a solution of 1.22 g (8.71 mmol) of ethyl 1 H-imidazole-2-carboxylate (ref) in a mixture of tetrahydrofurane (20 mL) and water (20 mL). The reaction mixture was warmed up to reflux, and stirred for 1.5 hours. The reaction mixture was cooled to room temperature and the solvent was evaporated under vacuum. The crude residue (3.0 g) was used in next step without further purification.LRMS (m/z): 1 13 (M+1 )+.
	With water; lithium hydroxide; In tetrahydrofuran; for 1.5h;Reflux;	PREPARATION 321H-imidazole-2-carboxylic acid21.75 mL (43.5 mmol) of a 2M solution of lithium hydroxide in water were added to a solution of 1.22 g (8.71 mmol) of <strong>[33543-78-1]ethyl 1H-imidazole-2-carboxylate</strong> (ref) in a mixture of tetrahydrofurane (20 mL) and water (20 mL).The reaction mixture was warmed up to reflux, and stirred for 1.5 hours.The reaction mixture was cooled to room temperature and the solvent was evaporated under vacuum.The crude residue (3.0 g) was used in next step without further purification.LRMS (m/z): 113 (M+1)+.

References: [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 409 - 411.
[2]Patent: WO2012/146666,2012,A1 .Location in patent: Page/Page column 118.
[3]Patent: EP2518070,2012,A1 .Location in patent: Page/Page column 52.

2
[ 33543-78-1 ]
[ 74840-99-6 ]

References: [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 409 - 411.

3
[ 33543-78-1 ]
[ 58752-31-1 ]
1-((6aR,9R,10aR)-7-Methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl)-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 1463 - 1473.

4
[ 33543-78-1 ]
[ 96737-35-8 ]
1-((6aR,9S,10aR)-7-Methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl)-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Chemical and Pharmaceutical Bulletin,1994,vol. 42,p. 2042 - 2048.

5
[ 64-17-5 ]
[ 163769-73-1 ]
[ 33543-78-1 ]

Yield	Reaction Conditions	Operation in experiment
64.3%	With sulfuric acid; at 20℃;Reflux;	The above-obtained residue was dissolved in EtOH (300 mL). To this solution, cone. H2S04 (98percent, 30 mL, 522 mmol, 2.76 eq) was added dropwise while keeping the reaction temperature below 25 °C. The resulting mixture was stirred at reflux for 7 h and then stirred at RT overnight. The mixture was concentrated in vacuo to remove EtOH. The resulting suspension was diluted with ice -water (200 mL) and neutralized with concentrated ammonium hydroxide to adjust the pH to 5-6 while keeping the temperature below 5 °C. The solid was collected by filtration, rinsed with water (10 mL x 3), and dried in vacuo to afford the first batch of crude product (10 g). The filtrate was extracted with ethyl acetate (200 mL x 2). The combined organic layer was washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo. The resulting residue was combined with the first batch crude product and then re-crystallized in isopropyl ether to afford ethyl lH-imidazole- 2-carboxylate (18 g, 64.3percent yield ).
		The above-obtained residue (C-2) is dissolved in EtOH (300 mL). To this solution, cone. H2S04 (98percent, 30 mL, 522 mmol, 2.76 eq) is added dropwise while keeping the reaction temperature below 25 °C. The resulting mixture is stirred at reflux for 7 h and then stirred at RT overnight. The mixture is concentrated in vacuo to remove EtOH. The resulting suspension is diluted with ice-water (200 mL) and neutralized with concentrated ammonium hydroxide to adjust the pH to 5-6 while keeping the temperature below 5 °C. The solid is collected by filtration, rinsed with water (10 mL x 3), and dried in vacuo to afford a first portion of the product. The filtrate is extracted with ethyl acetate (200 mL x 2). The combined organic layers are washed with brine, dried over Na2S04 and filtered. The filtrate is concentrated in vacuo. The resulting residue is combined with the first portion of product and then recrystallized in isopropyl ether to afford the product, ethyl lH-imidazole-2-carboxylate (C-3).

References: [1]Patent: WO2013/12915,2013,A1 .Location in patent: Paragraph 00945.
[2]Journal of Organic Chemistry,1995,vol. 60,p. 1090 - 1092.
[3]Patent: WO2011/146882,2011,A1 .Location in patent: Page/Page column 108-109.

6
[ 33543-78-1 ]
[ 161801-95-2 ]
[ 161801-88-3 ]

References: [1]Heterocycles,1999,vol. 50,p. 259 - 267.

7
[ 33543-78-1 ]
[ 172901-77-8 ]
[ 172901-74-5 ]

References: [1]Heterocycles,1999,vol. 50,p. 259 - 267.

8
[ 33543-78-1 ]
[ 1056246-70-8 ]
[ 172901-73-4 ]

References: [1]Heterocycles,1999,vol. 50,p. 259 - 267.

9
[ 33543-78-1 ]
[ 132993-66-9 ]
[ 161801-89-4 ]

References: [1]Heterocycles,1999,vol. 50,p. 259 - 267.

10
[ 33543-78-1 ]
[ 1775-27-5 ]
ethyl 1-(1-oxo-2,3-dihydro-1H-inden-2-yl)-1H-imidazole-2-carboxylate [ No CAS ]

References: [1]Heterocycles,1999,vol. 50,p. 259 - 267.

Yield	Reaction Conditions	Operation in experiment
		3.78 g of 3-(2-cyanomethylphenyl)propanoic acid are added to a solution of 3 ml of thionyl chloride and 15 ml of dichloromethane. After 0.55 ml of dimethylformamide is added, the reaction medium is heated at 30° C. for 4 hours. Evaporation of the medium leads to an orange-coloured oil. This oil is solubilized in 25 ml of 1,2-dichloroethane, and is then added dropwise at 10° C. under an argon atmosphere to a solution of 8 g of aluminium chloride and 35 ml of 1,2-dichloroethane. After 18 hours of reaction at a temperature close to 20° C., the reaction medium is poured over 60 g of ice. The solution is then decanted and the aqueous phase is extracted with 50 ml of dichloromethane.

13
[ 33543-78-1 ]
[ 3199-69-7 ]
[ 156484-56-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 591 - 596.

14
[ 33543-78-1 ]
[ 29278-11-3 ]
1-(5-methoxy-1-oxo-indan-2-yl)-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 591 - 596.

15
[ 33543-78-1 ]
[ 55144-54-2 ]
[ 156484-52-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 591 - 596.

16
[ 33543-78-1 ]
[ 54714-53-3 ]
[ 156484-54-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 591 - 596.

17
[ 33543-78-1 ]
[ 54714-54-4 ]
[ 156484-48-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 591 - 596.

18
[ 33543-78-1 ]
[ 156484-68-3 ]
[ 156484-67-2 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; water;	the solution of 5.3 g of <strong>[33543-78-1]ethyl imidazole-2-carboxylate</strong> in 20 ml of anhydrous dimethylformamide is added dropwise over 30 minutes at a temperature close to 20° C. to a suspension of 2.43 g of 50percent sodium hydride in 60 ml of anhydrous dimethylformamide kept under a nitrogen atmosphere. After stirring for 15 minutes, a solution of 9.26 g of 2-bromo-4-fluoro-1-indanone in 25 ml of anhydrous dimethylformamide is added dropwise over 30 minutes at a temperature close to 20° C. The mixture is stirred for 18 hours, and then after slowly adding 30 ml of water, poured into 200 ml of distilled water and extracted four times with 100 ml of dichloromethane. The organic phases are pooled, washed with 600 ml of distilled water, dried over anhydrous sodium sulphate and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 45° C. The residue thus obtained is purified by flash chromatography on a silica column, under a nitrogen stream at medium pressure (0.5 bar) with ethyl acetate as eluent. 1.2 g of ethyl 1-(4-fluoro-1-oxo-2-indanyl)imidazole-2-carboxylate are thus obtained which melt at 145° C.

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 591 - 596.
[2]Patent: US5677306,1997,A .

19
[ 33543-78-1 ]
[ 111538-45-5 ]
[ 156484-46-7 ]

Yield	Reaction Conditions	Operation in experiment
	In N-methyl-acetamide; chloroform; water;	a solution of 13.3 g of <strong>[33543-78-1]ethyl imidazole-2-carboxylate</strong> in 145 ml of anhydrous dimethylformamide is added dropwise over 20 minutes at a temperature of between 20° C. and 25° C. to a suspension of 3.4 g of 80percent sodium hydride in 45 ml of anhydrous dimethylformamide maintained under a nitrogen atmosphere. After stirring for 15 minutes, a solution of 26 g of 2-bromo-5-fluoro-1-indanone in 190 ml of anhydrous dimethylformamide is added dropwise over 10 minutes at the same temperature. The mixture is stirred for 1 hour 30 minutes and then, after slow addition of 100 ml of water, poured over 3800 ml of distilled water and extracted 4 times with a total of 3800 ml of chloroform. The organic extracts are pooled, washed with 950 ml of distilled water, dried over anhydrous sodium sulphate and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 40° C. The product obtained (27 g) is chromatographed on 1490 g of neutral silica gel (0.020-0.045 mm) contained in a column 9.6 cm in diameter, eluding under pressure with a dichloromethane-ethyl acetate mixture (70-30 by volume) and collecting 80 ml fractions. Fractions 13 to 70 are pooled and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 40° C. 13.4 g of ethyl 1-(5-fluoro-1-oxo-2-indanyl)imidazole-2-carboxylate are thus obtained which melt at 127° C. The 2-bromo-5-fluoro-1-indanone can be prepared in the following manner:

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 591 - 596.
[2]Patent: US5677306,1997,A .

20
[ 33543-78-1 ]
[ 127425-72-3 ]
[ 156484-65-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide; In ethanol; dichloromethane;	a solution of 9.5 g of <strong>[33543-78-1]ethyl imidazole-2-carboxylate</strong>, 9.9 g of 2,5-dibromo-1-indanone and 0.1 g of sodium iodide in 280 ml of ethanol is kept boiling for 16 hours, cooled to 20° C. and dried under reduced pressure (20 mmHg; 2.6 kPa) at 50° C. The product obtained (21 g) is dissolved in 50 ml of dichloromethane and the solution is washed 3 times with a total of 600 ml of distilled water, dried over anhydrous magnesium sulphate and dried under reduced pressure (20 mmHg; 2.6 kPa) at 50° C. The product obtained (12.7 g) is chromatographed on 790 g of neutral silica gel (0.020-0.045 mm) contained in a column 7 cm in diameter, eluding under pressure with a dichloromethane-ethyl acetate mixture (70-30 by volume) and collecting 75-ml fractions. Fractions 70 to 140 are pooled and concentrated to dryness under reduced pressure (15 mmHg; 2 kPa) at 40° C. 3.7 g of ethyl 1-(5-bromo-1-oxo-2-indanyl)imidazole-2-carboxylate are thus obtained which melt at 140° C. The 2,5-dibromo-1-indanone can be prepared as described in European Patent 346107.

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 591 - 596.
[2]Patent: US5677306,1997,A .

21
[ 33543-78-1 ]
[ 156484-83-2 ]
[ 156484-82-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 591 - 596.

22
[ 33543-78-1 ]
[ 112812-23-4 ]
[ 156484-61-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 591 - 596.

23
[ 33543-78-1 ]
[ 173252-61-4 ]
[ 173252-60-3 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; ethyl acetate;	4-Acetamido-2-(2-ethoxycarbonyl-1H-imidazol-1-yl)indanone can be prepared according to the following protocol: 14.87 g of <strong>[33543-78-1]ethyl 1H-imidazole-2-carboxylate</strong> and 14.14 g of 4-acetamido-2-bromoindanone (65percent pure) are heated at 110° C. for 15 minutes. After cooling to a temperature in the region of 20° C., the crude product is purified by flash chromatography on a silica column, using ethyl acetate and then a mixture of ethyl acetate and methanol (90/10 by volume) as eluents. 4.34 g of the expected product are thus isolated in the form of a greenish-grey solid melting at 160° C.

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 591 - 596.
[2]Patent: US5789406,1998,A .

24
[ 33543-78-1 ]
[ 98709-68-3 ]
[ 173252-80-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 2749 - 2754.

25
[ 33543-78-1 ]
[ 173252-90-9 ]
[ 173252-89-6 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	a mixture of 3.92 g of <strong>[33543-78-1]ethyl imidazole-2-carboxylate</strong> and 3.4 g of 2-bromo-4-cyano-1-indanone is heated at 130° C. for 20 minutes, cooled to 20° C. and dissolved in 20 ml of dichloromethane. The mixture is then concentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 40° C. The residue thus obtained is purified by flash chromatography on a silica column, under a nitrogen stream at medium pressure (0.5 bar), with a dichloromethane/methanol (95/5 by volume) mixture as eluent. 1.5 g of ethyl 1-[(4-cyano-1-oxoindan-2-yl)]imidazole-2-carboxylate are thus obtained, which product melts at 159° C. 2-Bromo-4-cyano-1-indanone can be obtained in the following way:

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 2749 - 2754.
[2]Patent: US5902803,1999,A .

26
[ 33543-78-1 ]
[ 183735-02-6 ]
[ 183734-99-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 2749 - 2754.

27
[ 33543-78-1 ]
[ 183734-96-5 ]
[ 183734-95-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 2749 - 2754.

28
[ 33543-78-1 ]
[ 24424-99-5 ]
N-Boc-2-ethoxycarbonylimidazole [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2003,vol. 40,p. 159 - 162.

29
[ 623-73-4 ]
[ 33543-78-1 ]
1-ethoxycarbonylmethylimidazol-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2004,vol. 60,p. 9391 - 9396.

30
[ 33543-78-1 ]
C₂₆H₂₁N₂O₂S^(1-)*Na⁽¹⁺⁾ [ No CAS ]
1-(biphenyl-4-yl-phenyl-methyl)-1H-imidazole-2-carboxylic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,2004,vol. 60,p. 9391 - 9396.

31
[ 33543-78-1 ]
[ 329984-05-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	With (2-trimethylethylsilylethoxy)methyl chloride; potassium carbonate; In acetone; at 20℃; for 10h;	A flask charged with <strong>[33543-78-1]1H-<strong>[33543-78-1]imidazole-2-carboxylic acid ethyl ester</strong></strong> (1.03 g, 7.36 mmol), K2CO3 (2.00 g, 14.5 mmol), SEM-Cl (1.56 mL, 8.89 mmol), and 20 mL of acetone was stirred for 10 h at RT. The reaction was diluted with EtOAc (100 mL), washed with NaHCO3 (2.x.100 mL), brine (100 mL), and the organic layer dried over Na2SO4 and concentrated. The title compound was eluted from a 20-g SPE with 50percent EtOAc/hexanes to give 1.50 g (76percent) of a colorless oil. Mass spectrum (ESI, m/z): Calcd. for C12H22N3O3Si, 271.1 (M+H), found 271.1

References: [1]Patent: US2007/249649,2007,A1 .Location in patent: Page/Page column 64.

32
[ 33543-78-1 ]
[ 76513-69-4 ]
[ 329984-05-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With sodium hydride; In N,N-dimethyl-formamide; at 0 - 25℃; for 12h;Inert atmosphere;	SEM-Cl (18.98 mL, 107.04 mmol) was added to ethyl lH-imidazole-2-carboxylate (10 g, 71.36 mmol) and NaH (4.28 g, 107 mmol) in DMF (50 mL) at 0°C under nitrogen. The resulting mixture was then stirred at 25 °C for 12 hours. The reaction mixture was quenched with water (50 mL), extracted with EtOAc (2 x 100 mL), the organic layer was dried over Na2S04, filtered and evaporated to afford a yellow residue. The crude product was purified by flash silica chromatography, elution gradient 30 to 70percent EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford ethyl 1 -((2- (trimethylsilyl)ethoxy)methyl)-lH-imidazole-2-carboxylate (Intermediate 16; 20 g, 100percent) as a yellow oil. H NMR (400 MHz, DMSO, 30 °C) delta 0.00 (9H, s), 0.03 - 0.08 (2H, m), 1.37 (3H, t), 3.53 - 3.62 (2H, m), 4.37 (2H, q), 5.76 (2H, s), 7.18 (1H, d), 7.68 (1H, d). m/z: ES+ [M+H]+ 271
76%	With potassium carbonate; In acetone; at 20℃; for 10h;	a) 1-(2-Trimethylsilanyl-ethoxymethyl)-<strong>[33543-78-1]1H-<strong>[33543-78-1]imidazole-2-carboxylic acid ethyl ester</strong></strong> A flask charged with <strong>[33543-78-1]1H-<strong>[33543-78-1]imidazole-2-carboxylic acid ethyl ester</strong></strong> (1.03 g, 7.36 mmol), K2CO3 (2.00 g, 14.5 mmol), SEM-Cl (1.56 mL, 8.89 mmol), and 20 mL of acetone was stirred for 10 h at RT. The reaction was diluted with EtOAc (100 mL), washed with NaHCO3 (2*100 mL), brine (100 mL), and the organic layer dried over Na2SO4 and concentrated. The title compound was eluted from a 20-g SPE with 50percent EtOAc/hexanes to give 1.50 g (76percent) of a colorless oil. Mass spectrum (ESI, m/z): Calcd. for C12H22N3O3Si, 271.1 (M+H), found 271.1.
70%	With potassium carbonate; In N,N-dimethyl-formamide; at 0 - 20℃;	Synthesis of Ethyl 1~((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2- carboxylate (lnt~1a) ciInMa2-(Trimethylsilyl)ethoxymethyi chloride (12.8 g, 0.077 mol) was added to a stirred solution of <strong>[33543-78-1]ethyl imidazole-2-carboxylate</strong> (9.0 g, 0.064 mol) and potassium carbonate (17.7 g, 0.128 mol) in NtN-dimethylformamide (50 mL) at 0 °C. The mixture was allowed to stir from 0 °C to r.t. overnight. Water and ethyl acetate were added and the layers were separated. The separated aqueous layer was extracted with ethyl acetate (X2). The combined organic layers were washed with water (X2). The separated organic layer was dried (MgS04) and filtered. The solvents were removed in vacuo andchromatographic purification (ethyl acetate - hexane) of the residue gave imidazole InMa (12 g, 70percent) as a colorless oil. LCMS m/e (M + H+) - 271.1.

With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 1h;Inert atmosphere;

SEMCI (1.519 ml_, 8.56 mmol) was added to a DMF (10 mL) suspension of K2C03 (1.972 g, 14.27 mmol) and [33543-78-1]ethyl imidazole-2-carboxylate (CAS 33543-78-1 ) (1 g, 7.14 mmol). After the mildly exothermic reaction subsided, the mixture was allowed to stir one hour at room temperature and was quenched with the addition of water and ethyl acetate. The organic phase was washed with water, brine, dried (sodium sulfate), filtered and concentrated. Purification of the residue by FCC (100percent Heptane to 50percent ethyl acetate/Heptane) afforded the title compound. MS (ESI+) m/z 271.4 (M+H).

References: [1]Patent: WO2017/80979,2017,A1 .Location in patent: Page/Page column 98; 110.
[2]Patent: US2007/249593,2007,A1 .Location in patent: Page/Page column 59.
[3]Patent: WO2011/149874,2011,A2 .Location in patent: Page/Page column 51-52.
[4]Patent: WO2015/9977,2015,A1 .Location in patent: Page/Page column 127.

33
[ 33543-78-1 ]
[ 865998-46-5 ]

References: [1]Synthetic Communications,2014,vol. 44,p. 968 - 975.
[2]Patent: WO2006/89664,2006,A2 .Location in patent: Page/Page column 14; 23.
[3]Patent: WO2005/92865,2005,A1 .Location in patent: Page/Page column 33.

34
[ 865998-45-4 ]
[ 33543-78-1 ]

References: [1]Synthetic Communications,2014,vol. 44,p. 968 - 975.
[2]Patent: WO2006/89664,2006,A2 .Location in patent: Page/Page column 22; 23.
[3]Patent: WO2005/92865,2005,A1 .Location in patent: Page/Page column 32-33.

35
[ 33543-78-1 ]
[ 327188-52-3 ]
[ 327188-91-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide;	EXAMPLE 69 A mixture of 2-chloro-4-(4-chlorophenyl)-5-[3-(2-methoxyphenoxy)propyl]oxazole (1.00 g), ethyl 2-imidazolecarboxylate (990 mg), potassium carbonate (1.38 g) and N,N-dimethylformamide (10 ml) was stirred at 120-130° C. for 1 hour. The reaction mixture was poured into water (100 ml), and the resulting solid precipitate was filtered, air-dried and recrystallized from acetone-isopropyl ether to give ethyl 1-[4-(4-chlorophenyl)-5-[3-(2-methoxyphenoxy)propyl]-2-oxazolyl]imidazole-2-carboxylate as pale yellow prisms (290 mg, 23percent). Melting point 90-91° C.

References: [1]Patent: US6605629,2003,B1 .

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Technical Information

• Acyl Group Substitution • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents

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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

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

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CAS No.: 33543-78-1

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CAS No.: 33543-78-1

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