Tetrahydrofuran → 2-Azido-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid

HRID 1667674Notes

Reaction equation

HRID 1667674 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]([N:11]=[N+:12]=[N-:13])=[N:8][C:7]=1[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)=[O:5])C.O1CCCC1.O.[OH-].[Li+]>O.C(OCC)C>[N:11]([C:9]1[S:10][C:6]([C:4]([OH:5])=[O:3])=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=2)[N:8]=1)=[N+:12]=[N-:13]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 866428012-Azido-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 866428022-Azido-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acidYield 79.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 3.0 g (8.76 mmole) of 2-azido-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid ethyl ester, 54 mL of tetrahydrofuran was added 3.71 g (88.3 mmole) of lithium hydroxide monohydrate in 36 mL of water. The mixture was stirred at room temperature for 3 hours, and then diluted with 350 mL of diethyl ether. The mixture was extracted three times with 100 mL of water. The combined aqueous layers were acidified by addition of 1M hydrochloric acid, and extracted three times with 100 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 2.20 g of 2-azido-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid as a yellow-orange solid.

Workup

  1. extractionThe mixture was extracted three times with 100 mL of water
  2. additionThe combined aqueous layers were acidified by addition of 1M hydrochloric acid
  3. extractionextracted three times with 100 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-72965b1a00df4a8f8f1269f03a88ef44
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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