HCID 20376598, compound → HCID 20376640, compound

HRID 2052428Notes

Reaction equation

HRID 2052428 reaction equation
[CH3:1][N:2]([CH3:19])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:7]=1[C:15]([F:18])([F:17])[F:16])(=[O:5])=[O:4]>C(O)(=O)C.[Fe]>[CH3:1][N:2]([CH3:19])[S:3]([C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:7]=1[C:15]([F:17])([F:16])[F:18])(=[O:4])=[O:5]

Participants

4

Reactant 1

HCID 20376598HCID 20376598, compound

Product 1

HCID 20376640HCID 20376640, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a heated mixture containing 13.5 g (0.045 mole) of the amide prepared as in (b) above in 250 ml of 5% acetic acid was added portionwise and with stirring 12 g of iron powder. The mixture was refluxed for 1/2 hour. The mixture was filtered while hot and the cooled filtrate was extracted with ether. The ether extract was washed with aqueous sodium bicarbonate, dried, concentrated and recrystallized from ether-hexane (1:2) to give 10.1 g (83%) of product as a colorless solid; m.p. 140°-142° C.

Workup

  1. additionTo a heated mixture containing
  2. additionwas added portionwise
  3. temperatureThe mixture was refluxed for 1/2 hour
  4. filtrationThe mixture was filtered while hot and the cooled filtrate
  5. extractionwas extracted with ether
  6. extractionThe ether extract
  7. washwas washed with aqueous sodium bicarbonate
  8. customdried
  9. concentrationconcentrated
  10. customrecrystallized from ether-hexane (1:2)

Sources & evidence

ORD record
ord-73f19cbe08e4459b8ffaec8296236431
Source dataset
uspto-grants-1980_01
Patent number
US04184867

Reaction notes

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