4-Nitro-1-[(propan-2-yl)sulfanyl]-2-(trifluoromethyl)benzene → HCID 20376627, compound

HRID 2052424Notes

Reaction equation

HRID 2052424 reaction equation
[CH:1]([S:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])([CH3:3])[CH3:2]>C(O)(=O)C>[CH:1]([S:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[C:14]([F:17])([F:15])[F:16])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 123270534-Nitro-1-[(propan-2-yl)sulfanyl]-2-(trifluoromethyl)benzene

Product 1

HCID 20376627HCID 20376627, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture containing 132.5 g (0.5 mole) of the nitro compound prepared as in (a) above, in 800 ml of 5% aqueous acetic acid was heated to reflux with stirring. The heat mantle was removed and 150 g of powdered iron was added at such a rate as to maintain reflux. After completion of the addition, the mixture was stirred and refluxed for one hour, and filtered while hot. The filtrate was extracted with ether (3×300 ml). The combined extracts were washed with 10% sodium carbonate, and then with water. The dried solution was concentrated to dryness under reduced pressure to give 70.5 g (60%) of product as a yellow oil.

Workup

  1. additionA mixture containing
  2. temperaturewas heated
  3. temperatureto reflux
  4. customThe heat mantle was removed
  5. addition150 g of powdered iron was added at such a rate as
  6. temperatureto maintain
  7. temperaturereflux
  8. additionAfter completion of the addition
  9. stirringthe mixture was stirred
  10. temperaturerefluxed for one hour
  11. filtrationfiltered while hot
  12. extractionThe filtrate was extracted with ether (3×300 ml)
  13. washThe combined extracts were washed with 10% sodium carbonate
  14. concentrationThe dried solution was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-917ca80f572e466e8fba94cfb1fdfdd5
Source dataset
uspto-grants-1980_01
Patent number
US04184867

Reaction notes

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