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

HRID 1111370Notes

Reaction equation

HRID 1111370 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

Conditions

Temperature
20 °C

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 1N 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 1N 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-9e0a47f1d6f042e6b0a50b5154782c04
Source dataset
uspto-grants-1990_12
Patent number
US04980356

Reaction notes

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