2-Amino-6-(trifluoromethyl)benzothiazole → N-(6-trifluoromethylbenzothiazol-2-yl)-2-chloro-6-fluorobenzamide

HRID 653062Notes

Reaction equation

HRID 653062 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4](Cl)=[O:5].[NH2:12][C:13]1[S:14][C:15]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:16]=2[N:17]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[F:25][C:22]([F:23])([F:24])[C:20]1[CH:19]=[CH:18][C:16]2[N:17]=[C:13]([NH:12][C:4](=[O:5])[C:3]3[C:7]([F:11])=[CH:8][CH:9]=[CH:10][C:2]=3[Cl:1])[S:14][C:15]=2[CH:21]=1

Participants

5

Reactant 2

HCID 27359552-Amino-6-(trifluoromethyl)benzothiazoleHCID 27365472-Chloro-6-fluorobenzoyl chloride

Product 1

HCID 13798347N-(6-trifluoromethylbenzothiazol-2-yl)-2-chloro-6-fluorobenzamideYield 66.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

At 0 to 5° C., 2-chloro-6-fluorobenzoyl chloride (1.93 g) was added dropwise to a solution composed of 2-amino-6-trifluoromethylbenzothiazole (2.18 g), pyridine (30 ml) and 4-dimethylaminopyridine (0.1 g). The reaction mixture was stirred at room temperature (20 to 30° C.) for one day, and then the pyridine was evaporated. Water was added to the residue, and the mixture was stirred. The resulting crystals were collected by filtration, and thoroughly washed with water. Recrystallization from ethanol gave the desired N-(6-trifluoromethylbenzothiazol-2-yl)-2-chloro-6-fluorobenzamide (2.5 g).

Workup

  1. customthe pyridine was evaporated
  2. additionWater was added to the residue
  3. stirringthe mixture was stirred
  4. filtrationThe resulting crystals were collected by filtration
  5. washthoroughly washed with water
  6. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-9d849a59ec7c421cba41c69e61a65a96
Source dataset
uspto-grants-1987_06
Patent number
US04675331

Reaction notes

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