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

HRID 1111362Notes

Reaction equation

HRID 1111362 reaction equation
[NH:1]=[C:2]1[N:6]([CH2:7][CH2:8][OH:9])[C:5]2[CH:10]=[CH:11][C:12]([O:14][C:15]([F:18])([F:17])[F:16])=[CH:13][C:4]=2[S:3]1.NC1SC2C=C(OC(F)(F)F)C=CC=2N=1.[Br:34]CCO>C(O)C>[BrH:34].[NH:1]=[C:2]1[N:6]([CH2:7][CH2:8][OH:9])[C:5]2[CH:10]=[CH:11][C:12]([O:14][C:15]([F:18])([F:16])[F:17])=[CH:13][C:4]=2[S:3]1

Participants

5

Reactant 3

HCID 5070RiluzoleHCID 108982-BromoethanolHCID 30762523-(2-Hydroxyethyl)-2-imino-6-trifluoromethoxybenzothiazoline

Product 1

HCID 30762513(2H)-Benzothiazoleethanol, 2-imino-6-(trifluoromethoxy)-, monohydrobromide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

2-(2-Imino-6-trifluoromethoxy-3-benzothiazolinyl)ethanol may be prepared according to the following process: 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 then cooled to a temperature in the region of 20° C. The precipitate formed is filtered off and washed with ethyl ether (100 cc). 2-(2-Imino-6-trifluoromethoxy-3-benzothiazolinyl)ethanol hydrobromide (6.4 g), m.p. 219° C., is obtained.

Workup

  1. customThe precipitate formed
  2. filtrationis filtered off
  3. washwashed with ethyl ether (100 cc)

Sources & evidence

ORD record
ord-38302625627d475db494fbbe6af75b31
Source dataset
uspto-grants-1990_12
Patent number
US04980356

Reaction notes

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