Iodoacetamide → 2-[2-Imino-6-(trifluoromethoxy)-1,3-benzothiazol-3(2H)-yl]ethanimidic acid

HRID 1494411Notes

Reaction equation

HRID 1494411 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.I[CH2:17][C:18]([NH2:20])=[O:19]>C(C(C)=O)C>[NH:1]=[C:2]1[N:6]([CH2:17][C:18]([NH2:20])=[O: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 3727IodoacetamideHCID 5070Riluzole

Product 1

HCID 30764122-[2-Imino-6-(trifluoromethoxy)-1,3-benzothiazol-3(2H)-yl]ethanimidic acidYield 53%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The procedure is as in Example 15, starting with 2-amino-6-trifluoromethoxybenzothiazole (9.4 g) and iodoacetamide (14.8 g) in methyl ethyl ketone (50 cc). The mixture is heated for 18 hours to boiling and then cooled to a temperature in the region of 20.C. The precipitate formed is filtered off, then added to distilled water (100 cc) and treated with IN sodium hydroxide (37 cc). The insoluble matter is filtered off, washed with distilled water (100 cc) and recrystallized in boiling methanol (100 cc). (2-Imino-6-trifluoromethoxy-3-benzothiazolinyl)acetamide (6.2 g), m.p. 228° C., is obtained.

Workup

  1. temperatureThe mixture is heated for 18 hours
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. additionadded
  5. distillationto distilled water (100 cc)
  6. additiontreated with IN sodium hydroxide (37 cc)
  7. filtrationThe insoluble matter is filtered off
  8. washwashed with distilled water (100 cc)
  9. customrecrystallized

Sources & evidence

ORD record
ord-57ce784e5da44225a5279cacdcf53993
Source dataset
uspto-grants-1991_06
Patent number
US05026717

Reaction notes

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