Methanol → 2-Amino-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide

HRID 1667668Notes

Reaction equation

HRID 1667668 reaction equation
[N:1]([C:4]1[S:5][C:6]([C:19]([NH2:21])=[O:20])=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:8]=1)=[N+]=[N-].CO.[Cl-].[NH4+]>[Zn].O1CCCC1>[NH2:1][C:4]1[S:5][C:6]([C:19]([NH2:21])=[O:20])=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([C:15]([F:18])([F:16])[F:17])=[CH:13][CH:14]=2)[N:8]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 866428002-Azido-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide

Product 1

HCID 593753612-Amino-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amideYield 101.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.6727 g (2.147 mmole) of 2-azido-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide, 20 mL of methanol and 20 mL of tetrahydrofuran was added 1.42 g (21.8 mg-atom) of zinc and 2.84 g (53.1 mmole) of ammonium chloride. The mixture was stirred vigorously for 1 hour and then filtered through Diatomaceous earth, washing the pad with methanol and tetrahydrofuran. The filtrate was concentrated under reduced pressure and then diluted with 350 mL of ethyl acetate, washed three times with 75 mL of water, once with brine, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure to give 0.6276 g of 2-amino-4-(4-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide (V.47) as an off-white solid.

Workup

  1. filtrationfiltered through Diatomaceous earth
  2. washwashing the pad with methanol and tetrahydrofuran
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additiondiluted with 350 mL of ethyl acetate
  5. washwashed three times with 75 mL of water
  6. dry with materialonce with brine, dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-37e01a384cc44012a03a862b7090abe3
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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