Riluzole → 3-Methyl-6-(trifluoromethoxy)-1,3-benzothiazol-2(3H)-imine

HRID 1111365Notes

Reaction equation

HRID 1111365 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.CI.[C:18](=O)([O-])O.[Na+]>C(O)C>[NH:1]=[C:2]1[N:6]([CH3:18])[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

5

Reactant 3

HCID 5070RiluzoleHCID 6328Methyl iodideHCID 516892Sodium Bicarbonate

Product 1

HCID 30763993-Methyl-6-(trifluoromethoxy)-1,3-benzothiazol-2(3H)-imineYield 27.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

2-Amino-6-trifluoromethoxybenzothiazole (7.1 g) and methyl iodide (4.3 g) in absolute ethanol (20 cc) are heated for 18 hours to boiling. The mixture is then cooled to a temperature in the region of 20° C. The precipitate formed is separated by filtration and washed with absolute ethanol (2×20 cc). The solid is taken up in distilled water (100 cc) heated to 60° C., and the solution obtained is treated with sodium hydrogen carbonate (2.6 g). The precipitate is separated by filtration and recrystallized in a boiling mixture (50 cc) of absolute ethanol and distilled water (50:50 by volume). 2-Imino-3-methyl-6-trifluoromethoxybenzothiazoline (2.1 g), m.p. 60°-62° C., is obtained.

Workup

  1. customThe precipitate formed
  2. customis separated by filtration
  3. washwashed with absolute ethanol (2×20 cc)
  4. temperatureheated to 60° C.
  5. customthe solution obtained
  6. customThe precipitate is separated by filtration
  7. customrecrystallized in a boiling mixture (50 cc) of absolute ethanol
  8. distillationdistilled water (50:50 by volume)

Sources & evidence

ORD record
ord-5e7f95c88b2e4ba288a2d4b417987fd2
Source dataset
uspto-grants-1990_12
Patent number
US04980356

Reaction notes

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