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

HRID 1494409Notes

Reaction equation

HRID 1494409 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][CH:19]=[CH2:20]>CC(O)C>[BrH:16].[CH2:20]([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])[CH2:19][CH:18]=[CH2:17]

Participants

4

Reactant 2

HCID 5070RiluzoleHCID 21241Homoallyl bromide

Product 1

HCID 30764063-(But-3-en-1-yl)-6-(trifluoromethoxy)-1,3-benzothiazol-2(3H)-imine--hydrogen bromide (1/1)Yield 16.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The procedure is as in Example 15, starting with 2-amino-6-trifluoromethoxybenzothiazole (9.4 g) and 4-bromo-1butene (10.8 g) in 2-propanol (30 cc). The mixture is heated for 48 hours to boiling. After cooling of the mixture to a temperature in the region of 20.C, the precipitate is filtered off and then washed with 2-propanol (2×50 cc). 3(3-Butenyl)-2-imino-6-trifluoromethoxybenzothiazoline hydrobromide (2.5 g), m.p. 202° C., is obtained.

Workup

  1. temperatureThe mixture is heated for 48 hours
  2. filtrationthe precipitate is filtered off
  3. washwashed with 2-propanol (2×50 cc)

Sources & evidence

ORD record
ord-200b253be1ce4da6a25562ad2e25299a
Source dataset
uspto-grants-1991_06
Patent number
US05026717

Reaction notes

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