Ammonia → Riluzole

HRID 1164498Notes

Reaction equation

HRID 1164498 reaction equation
BrBr.[F:3][C:4]([F:14])([F:13])[O:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1.[S-:15][C:16]#[N:17].[K+].N>C(O)(=O)C.O>[NH2:17][C:16]1[S:15][C:11]2[CH:12]=[C:6]([O:5][C:4]([F:13])([F:14])[F:3])[CH:7]=[CH:8][C:9]=2[N:10]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 24408BromineHCID 516872Potassium thiocyanateHCID 6008484-(Trifluoromethoxy)aniline

Product 1

HCID 5070RiluzoleYield 69.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

A solution of 77 g of bromine in 220 ml of acetic acid is added drop by drop, in a period of one hour, to a solution of 84 g of 4-trifluoromethoxy-aniline and 187 g of potassium thiocyanate in 500 ml of acetic acid. The mixture is stirred overnight at the ambient temperature. The reaction mixture is then poured into 2 liters of water. The resulting mixture is cooled in an icebath and neutralized by addition of ammonia. The insoluble material is separated by filtration, washed with water, then recrystallized in an ethanol-water mixture (50--50). 77 g of 2-amino-6-trifluoromethoxy-benzothiazole, which melts at 119° C., are thus obtained.

Workup

  1. temperatureThe resulting mixture is cooled in an icebath
  2. customThe insoluble material is separated by filtration
  3. washwashed with water
  4. customrecrystallized in an ethanol-water mixture (50--50)

Sources & evidence

ORD record
ord-97bad8b1788e4e858b055f268ac33f4f
Source dataset
uspto-grants-1983_01
Patent number
US04370338

Reaction notes

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