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

HRID 1111373Notes

Reaction equation

HRID 1111373 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[Br:16][CH2:17][CH2:18][OH:19]>C(O)C>[BrH:16].[NH:1]=[C:2]1[N:6]([CH2:17][CH2:18][OH:19])[C:5]2[CH:7]=[CH:8][C:9]([O:11][C:12]([F:15])([F:13])[F:14])=[CH:10][C:4]=2[S:3]1

Participants

4

Reactant 2

HCID 5070RiluzoleHCID 108982-Bromoethanol

Product 1

HCID 30762513(2H)-Benzothiazoleethanol, 2-imino-6-(trifluoromethoxy)-, monohydrobromideYield 44.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

The procedure is as in Example 15, starting with 2-amino-6-trifluoromethoxybenzothiazole (9.4 g) and 2-bromoethanol (10 g) in absolute ethanol (30 cc). The mixture is heated for 95 hours to boiling and 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. temperatureThe mixture is heated for 95 hours
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with ethyl ether (100 cc)

Sources & evidence

ORD record
ord-3c8752774d9f4bb48c41f1aae61c6af4
Source dataset
uspto-grants-1990_12
Patent number
US04980356

Reaction notes

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