Isopropanol → N-(3-Methyl-4-nitro-1,2-thiazol-5-yl)ethanimidic acid

HRID 1591034Notes

Reaction equation

HRID 1591034 reaction equation
[Cl-].[NH4+].C(O)(C)C.[C:7]([NH:10][C:11]1[S:15][N:14]=[C:13]([CH2:16]C(=O)C2C=CC(Cl)=CC=2)[C:12]=1[N+:26]([O-:28])=[O:27])(=[O:9])[CH3:8]>O>[C:7]([NH:10][C:11]1[S:15][N:14]=[C:13]([CH3:16])[C:12]=1[N+:26]([O-:28])=[O:27])(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 25517Ammonium ChlorideHCID 19766006HCID 19766006, compound

Product 1

HCID 352525N-(3-Methyl-4-nitro-1,2-thiazol-5-yl)ethanimidic acidYield 70.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Reduced iron (2.94 grams, 50.0 mmol) and 0.30 gram of ammonium chloride were introduced into 20 ml of isopropyl alcohol and 3 ml of water, and the mixture was heated under reflux for 20 minutes. 5-Acetylamino-3-(4-chlorobenzoylmethyl)-4-nitroisothiazole (2.04 grams, 6.00 mmol) was added little by little, and the mixture was heated under reflux for 2 hours. The iron was removed by suction filtration, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated salt water and then dried over anhydrous sodium sulfate. After filtration, the solvent was removed by distillation under reduced pressure. The residue was dissolved in 20 ml of acetic acid and heated under reflux for 2 hours. The mixture was then poured into water and extracted with ethyl acetate. The extract was washed with aqueous bicarbonate and then with saturated salt water, and dried over anhydrous sodium sulfate. After filtration, the solvent was removed by distillation and the material was crystallized from ethyl acetate. Recovery was 1.23 gram (4.22 mmol); Yield was 70.3%; and Melting Point was 210° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 minutes
  3. temperaturewas heated
  4. temperatureunder reflux for 2 hours
  5. customThe iron was removed by suction filtration, water
  6. additionwas added
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe extract was washed with saturated salt water
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationAfter filtration
  11. customthe solvent was removed by distillation under reduced pressure
  12. dissolutionThe residue was dissolved in 20 ml of acetic acid
  13. temperatureheated
  14. temperatureunder reflux for 2 hours
  15. additionThe mixture was then poured into water
  16. extractionextracted with ethyl acetate
  17. washThe extract was washed with aqueous bicarbonate
  18. dry with materialwith saturated salt water, and dried over anhydrous sodium sulfate
  19. filtrationAfter filtration
  20. customthe solvent was removed by distillation
  21. customthe material was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-86098d9cf35a4243b8fa9ac3b9e62f42
Source dataset
uspto-grants-1993_04
Patent number
US05206129

Reaction notes

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