Riluzole → N-(6-trifluoromethoxybenzothiazol-2-yl)-2,6-difluorobenzamide

HRID 653063Notes

Reaction equation

HRID 653063 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[F:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[C:18]=1[C:19](Cl)=[O:20]>ClC1C=CC=CC=1>[F:14][C:12]([F:15])([F:13])[O:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:1][C:19](=[O:20])[C:18]3[C:17]([F:16])=[CH:25][CH:24]=[CH:23][C:22]=3[F:26])[S:3][C:4]=2[CH:10]=1

Participants

4

Reactant 2

HCID 5070RiluzoleHCID 874382,6-Difluorobenzoyl chloride

Product 1

HCID 13798350N-(6-trifluoromethoxybenzothiazol-2-yl)-2,6-difluorobenzamideYield 84.2%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture composed of 2-amino-6-trifluoromethoxybenzothiazole (2.34 g), 2,6-difluorobenzoylchloride (1.8 g) and chlorobenzene (20 ml) was boil for 1 hour. The hot reaction mixture was filtered and cooled to 10°-20° C. The resulting crystals were collected by filtration and washed with n-hexane (20 ml) to give N-(6-trifluoromethoxybenzothiazol-2-yl)-2,6-difluorobenzamide (3.15 g).

Workup

  1. filtrationThe hot reaction mixture was filtered
  2. temperaturecooled to 10°-20° C
  3. filtrationThe resulting crystals were collected by filtration
  4. washwashed with n-hexane (20 ml)

Sources & evidence

ORD record
ord-9493470ac99848179d21523125b80520
Source dataset
uspto-grants-1987_06
Patent number
US04675331

Reaction notes

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