Riluzole → 3(2H)-Benzothiazoleethanol, 2-imino-6-(trifluoromethoxy)-, monohydrobromide

HRID 1742628Notes

Reaction equation

FC(F)(F)C([N:5]=[C:6]1[N:10]([CH2:11][CH2:12][OH:13])[C:9]2[CH:14]=[CH:15][C:16]([O:18][C:19]([F:22])([F:21])[F:20])=[CH:17][C:8]=2[S:7]1)=O.NC1SC2C=C(OC(F)(F)F)C=CC=2N=1.[Br:40]CCO>C(O)C>[BrH:40].[NH:5]=[C:6]1[N:10]([CH2:11][CH2:12][OH:13])[C:9]2[CH:14]=[CH:15][C:16]([O:18][C:19]([F:22])([F:20])[F:21])=[CH:17][C:8]=2[S:7]1

Participants

Conditions

Temperature: 20 °C

Procedure

The 2-(2-imino-6-trifluoromethoxy-3-benzothiazolinyl)ethanol may be prepared according to the following process: 9.4 g of 2-amino-6-trifluoromethoxybenzothiazole and 10 g of 2-bromoethanol in 30 cm3 of absolute ethanol are heated at boiling temperature for 95 hours. The mixture is then cooled to a temperature in the region of 20° C. The precipitate formed is filtered and washed with 100 cm3 of ethyl ether. 6.4 g of 2-(2-imino-6-trifluoromethoxy-3-benzothiazolinyl)ethanol hydrobromide with a melting point of 219° C. are obtained.

Workup

customfor 95 hours
customThe precipitate formed
filtrationis filtered
washwashed with 100 cm3 of ethyl ether

Sources & evidence

ORD record: ord-7fb1bc6c119247c9ac956013e9770d42
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05340824

Reaction notes

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