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

HRID 1085126Notes

Reaction equation

[OH:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([O:13][C:14]([F:17])([F:16])[F:15])=[CH:12][C:7]=2[S:6][C:5]1=[NH:18].NC1SC2C=C(OC(F)(F)F)C=CC=2N=1.[Br:34]CCO>C(O)C>[BrH:34].[OH:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][C:11]([O:13][C:14]([F:16])([F:15])[F:17])=[CH:12][C:7]=2[S:6][C:5]1=[NH:18]

Participants

Conditions

Temperature: 20 °C

Procedure

3-(2-Hydroxyethyl)-2-imino-6-trifluoromethoxybenzothiazoline may be prepared in the following manner: 2-amino-6-trifluoromethoxybenzothiazole (9.4 g) and 2-bromoethanol (10 g) in absolute ethanol (30 cc) are heated for 95 hours to boiling. The mixture is cooled to a temperature in the region of 20° C. The precipitate formed is filtered off and washed with ethyl ether (100 cc). 3-(2-Hydroxyethyl)-2-imino-6-trifluoromethoxybenzothiazoline hydrobromide (6.4 g), m.p. 219° C., is thereby obtained.

Workup

customThe precipitate formed
filtrationis filtered off
washwashed with ethyl ether (100 cc)

Sources & evidence

ORD record: ord-93dd34b74fbb4f82beac53e36185ee27
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05008280

Reaction notes

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