Acetone → 2-Azido-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 1667673Notes

Reaction equation

HRID 1667673 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][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[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][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 33557Sodium AzideHCID 130418212-Chloro-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 866428012-Azido-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl esterYield 97.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 2.99 g (8.90 mmole) of 2-chloro-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester, 27 mL of acetone and 27 mL of water was added 2.97 g (45.15 mmole) of sodium azide. The mixture was heated at 70 degrees for 11 hours. The mixture was partitioned between 200 mL of ethyl acetate and 75 mL of water. The aqueous layer was extracted twice with 60 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 2.97 g of 2-azido-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester as a dark brown oil.

Workup

  1. temperatureThe mixture was heated at 70 degrees for 11 hours
  2. customThe mixture was partitioned between 200 mL of ethyl acetate and 75 mL of water
  3. extractionThe aqueous layer was extracted twice with 60 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-3f293fe2a97243f686c996c606289140
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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