Bromine → 5,7-Difluorobenzo[d]thiazol-2-amine

HRID 907709

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH2:12])=[S:11])[CH:5]=[C:6]([F:8])[CH:7]=1.BrBr>ClCCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]2[S:11][C:10]([NH2:12])=[N:9][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 10 °C

Procedure

To a suspension of N-(3,5-difluorophenyl) thiourea (3.40 g, 18.07 mmol) in DCE (95 mL) was added a solution of bromine in DCE (5 mL) below 30° C. The mixture was heated at reflux for 2.5 h, then cooled to 10° C., and the precipitate formed was collected by filtration and washed with DCE. The solid was stirred with water (200 mL), basified by treatment with conc. ammonium hydroxide, filtered, and dried in a vacuum oven to afford 5,7-difluoro-1,3-benzothiazol-2-amine (3.05 g, 90%). ret. time 2.18; m/z 187.1 (MH+) 1H NMR (400 MHz, DMSO-d6) δ 6.92 (m, 1H), 7.00 (m, 2H), 7.92 (s, 2H).

Workup

temperatureThe mixture was heated
temperatureat reflux for 2.5 h
customthe precipitate formed
filtrationwas collected by filtration
washwashed with DCE
filtrationfiltered
customdried in a vacuum oven

Sources & evidence

ORD record: ord-cff82a0362244790a89eafa798a1505e
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013166B2

Linked notes

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