Ammonium Chloride → HCID 19605497, compound

HRID 1603612Notes

Reaction equation

HRID 1603612 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([CH3:23])[CH:15]=2)(=[O:13])=[O:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[NH4+].[Cl-]>CO.O.[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([CH3:23])[CH:15]=2)(=[O:12])=[O:13])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 19605510HCID 19605510, compound

Product 1

HCID 19605497HCID 19605497, compoundYield 93.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

0.29 g (0.00086 mol) of 1-(3,5-dimethoxyphenylsulphonyl)-3-methyl-4-nitrobenzene was suspended in a mixture of 10 ml of methanol and 10 ml of water, treated with 0.30 g of iron powder and 0.30 g of NH4Cl and heated at reflux for 1.5 hrs. After cooling the mixture was diluted with 50 ml of methanol, treated in an ultrasound bath for a short time and suction filtered. The filter material was washed with a large amount of methanol and the filtrate was concentrated. The residue was suspended in water and treated in an ultrasound bath. The precipitate which thereby resulted was filtered off under suction and chromatographed on silica gel with ethyl acetate/hexane 1:1. There was obtained 0.246 g (92.5%) of 4-(3,5-dimethoxybenzenesulphonyl)-2-methyl-phenylamine as yellow coloured crystals; m.p.: 121-123° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1.5 hrs
  3. temperatureAfter cooling the mixture
  4. additiontreated in an ultrasound bath for a short time and suction
  5. filtrationfiltered
  6. washThe filter material was washed with a large amount of methanol
  7. concentrationthe filtrate was concentrated
  8. additiontreated in an ultrasound bath
  9. customThe precipitate which thereby resulted
  10. filtrationwas filtered off under suction
  11. customchromatographed on silica gel with ethyl acetate/hexane 1:1

Sources & evidence

ORD record
ord-1c2f50c9451c40bf86a046646cbfcd20
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

Loading…