Acetone → 2-Azido-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 1667665Notes

Reaction equation

HRID 1667665 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9](Cl)=[N:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)=[O:5])[CH3:2].CC(C)=O.[N-:26]=[N+:27]=[N-:28].[Na+]>O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([N:26]=[N+:27]=[N-:28])=[N:8][C:7]=1[C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 33557Sodium AzideHCID 674273002-Chloro-4-(4-trifluoromethylphenyl)thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 866427982-Azido-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl esterYield 99.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 2.41 g (7.18 mmole) of 2-chloro-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester, 2.4 mL of acetone and 2.4 mL of water was added 2.34 g (35.63 mmole) of sodium azide. The reaction mixture was heated at 70 degrees for 16 hours and then partitioned between 200 mL of ethyl acetate and 75 mL of water. The aqueous layer was extracted twice with 55 mL of ethyl acetate. The combined ethyl acetate layers were washed with 50 mL of brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 2.44 g of 2-azido-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester as a dark amber oil.

Workup

  1. temperatureThe reaction mixture was heated at 70 degrees for 16 hours
  2. custompartitioned between 200 mL of ethyl acetate and 75 mL of water
  3. extractionThe aqueous layer was extracted twice with 55 mL of ethyl acetate
  4. washThe combined ethyl acetate layers were washed with 50 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-123f6056890c459ea7ecb5ca51c4ec28
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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