Hydrogen Bromide → N-(7-acetylamino-4-methoxy-benzothiazol-2-yl)-benzamide

HRID 8349Notes

Reaction equation

[C:1]([NH:9][C:10](=[S:24])[NH:11][C:12]1[CH:13]=[C:14]([NH:20][C:21](=[O:23])[CH3:22])[CH:15]=[CH:16][C:17]=1[O:18][CH3:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.CS(C)=O>C(O)(=O)C>[C:21]([NH:20][C:14]1[C:13]2[S:24][C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:11][C:12]=2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=1)(=[O:23])[CH3:22]

Participants

Conditions

Temperature: 90 °C

Procedure

To a suspension of 15.0 g (43.7 mmol) N-[3-(3-benzoyl-thioureido)-4-methoxy-phenyl]-acetamide in 200 ml glacial acetic acid was added 7.65 ml (43.6 mmol) of a 5.7 M solution of HBr in acetic acid, and the mixture was heated at 90° C. for 1 h. 2.5 ml (48.0 mmol) DMSO was then added, and stirring continued at 90° C. for 1.5 h. After cooling to room temperature, the reaction mixture was poured onto 1000 ml distilled water, and the resulting slurry stirred for 15 min. The mixture was then filtered, and the filter cake washed with water, then dried in vacuo at 50° C., affording 12.8 g (86%) N-(7-acetylamino-4-methoxy-benzothiazol-2-yl)-benzamide as a light brown solid. ES-MS m/e (%): 342 (M+H+, 100).

Workup

temperatureAfter cooling to room temperature
additionthe reaction mixture was poured onto 1000 ml
distillationdistilled water
stirringthe resulting slurry stirred for 15 min
filtrationThe mixture was then filtered
washthe filter cake washed with water
customdried in vacuo at 50° C.

Sources & evidence

ORD record: ord-4a6aafb44c9c446da727d1d1bc6b81be
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087761B2

Reaction notes

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