Riluzole → 3-(Prop-2-en-1-yl)-6-(trifluoromethoxy)-1,3-benzothiazol-2(3H)-imine--hydrogen bromide (1/1)

HRID 1111366Notes

Reaction equation

HRID 1111366 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.[CH2:16]([Br:19])[CH:17]=[CH2:18]>C(O)C>[BrH:19].[CH2:18]([N:6]1[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][C:2]1=[NH:1])[CH:17]=[CH2:16]

Participants

4

Reactant 2

HCID 5070RiluzoleHCID 7841Allyl bromide

Product 1

HCID 30764043-(Prop-2-en-1-yl)-6-(trifluoromethoxy)-1,3-benzothiazol-2(3H)-imine--hydrogen bromide (1/1)Yield 28.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

The procedure is as in Example 15, starting with 2-amino-6-trifluoromethoxybenzothiazole (9.4 g) and allyl bromide (9.6 g) in absolute ethanol (30 cc). The mixture is heated for 48 hours to boiling. After cooling of the mixture to 0° C., the precipitate is filtered off, washed with ethyl ether (200 cc) and recrystallized in boiling 2-propanol (70 cc). 3-Allyl-2-imino-6-trifluoromethoxybenzothiazoline hydrobromide (4 g), m.p. 225° C., is obtained.

Workup

  1. temperatureThe mixture is heated for 48 hours
  2. filtrationthe precipitate is filtered off
  3. washwashed with ethyl ether (200 cc)
  4. customrecrystallized

Sources & evidence

ORD record
ord-3a9e3f37bc6241d890fd26c94e9a0ed7
Source dataset
uspto-grants-1990_12
Patent number
US04980356

Reaction notes

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