Ammonium Hydroxide → 3-(3-Trifluoromethylphenyl)-4-amino-5-isothiazolecarboxamide

HRID 67653Notes

Reaction equation

HRID 67653 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([C:9]2[C:13]([NH2:14])=[C:12]([C:15](O)=[O:16])[S:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1.C(N1C=CN=C1)([N:22]1C=CN=C1)=O.[OH-].[NH4+]>CN(C=O)C>[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([C:9]2[C:13]([NH2:14])=[C:12]([C:15]([NH2:22])=[O:16])[S:11][N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 54833AmflutizoleHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 130732603-(3-Trifluoromethylphenyl)-4-amino-5-isothiazolecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

One gram of 3-(3-trifluoromethylphenyl)-4-amino-5-isothiazolecarboxylic acid and 0.7 g. of carbonyldiimidazole were dissolved in 25 ml. of DMF at ambient temperature. The solution was stirred for 2.25 hours; 3 ml. of 14 N aqueous ammonium hydroxide were added and the resulting mixture stirred overnight at ambient temperature after which time it was poured into an ice-water mixture. 3-(3-Trifluoromethylphenyl)-4-amino-5-isothiazolecarboxamide formed in the above reaction precipitated and the precipitate was collected by filtration and was dried. 3-(3-Trifluoromethylphenyl)-4-amino-5-isothiazole carboxamide, thus prepared and purified, melted at about 124° C. after recrystallization from an ethyl acetate-hexane solvent mixture; yield 0.4 g.

Workup

  1. customat ambient temperature
  2. stirringthe resulting mixture stirred overnight at ambient temperature after which time it

Sources & evidence

ORD record
ord-a36c36c009f04a459759addbde33721b
Source dataset
uspto-grants-1982_08
Patent number
US04346094

Reaction notes

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