Hydrochloric Acid → 2-(5-Formyl-2-nitro-phenylamino)-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide

HRID 1667794Notes

Reaction equation

HRID 1667794 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:5]=[CH:6][C:7]([N+:29]([O-:31])=[O:30])=[C:8]([NH:10][C:11]2[S:12][C:13]([C:26]([NH2:28])=[O:27])=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[N:15]=2)[CH:9]=1.C(#N)C.Cl>O>[CH:3]([C:4]1[CH:5]=[CH:6][C:7]([N+:29]([O-:31])=[O:30])=[C:8]([NH:10][C:11]2[S:12][C:13]([C:26]([NH2:28])=[O:27])=[C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:23])([F:24])[F:25])[CH:17]=3)[N:15]=2)[CH:9]=1)=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 866428532-(5-Dimethoxymethyl-2-nitro-phenylamino)-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide

Product 1

HCID 866428542-(5-Formyl-2-nitro-phenylamino)-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amideYield 85.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.4154 g (0.861 mmole) of 2-(5-dimethoxymethyl-2-nitro-phenylamino)-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide, 16 mL of acetonitrile and 8 mL of 1M hydrochloric acid was heated at 60 degrees for 1.5 hours. The cooled mixture diluted with 50 mL of water. The precipitate was collected by filtration, washed with water and dried to give 0.3198 g of 2-(5-formyl-2-nitro-phenylamino)-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide (VI.48b) as an orange solid.

Workup

  1. temperaturewas heated at 60 degrees for 1.5 hours
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-949acf2ed7af4be9b37924bd1276409b
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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