HCID 57659246, compound → (RS)-S-(3-aminophenyl)-N-(isopropylcarbamoyl)-S-methylsulfoximide

HRID 38209Notes

Reaction equation

HRID 38209 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH3:19])(=[N:12][C:13](=[O:18])[NH:14][CH:15]([CH3:17])[CH3:16])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O>C(O)C.Cl.CO.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([S:10]([CH3:19])(=[N:12][C:13](=[O:18])[NH:14][CH:15]([CH3:16])[CH3:17])=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 1

HCID 57659246HCID 57659246, compound

Product 1

HCID 57659241(RS)-S-(3-aminophenyl)-N-(isopropylcarbamoyl)-S-methylsulfoximideYield 65%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

18.61 g iron powder in 198 ml ethanol and 1.93 ml conc. hydrochloric acid were stirred for 30 minutes at room temperature. 7.8 g (27.34 mmol) (RS)—S-(3-nitrophenyl)-N-(isopropylcarbamoyl)-S-methylsulfoximide in 20 ml methanol were added. The mixture was stirred at 60° C. for 2 hours and filtered over a bed of silica gel. The residue was washed with hot ethanol. The combined filtrates were evaporated. The crude residue was purified by column chromatography (silica gel, dichloromethane:dichloromethane/ethanol 1:1) to give 4.53 g (65% yield) of the title compound.

Workup

  1. filtrationfiltered over a bed of silica gel
  2. washThe residue was washed with hot ethanol
  3. customThe combined filtrates were evaporated
  4. customThe crude residue was purified by column chromatography (silica gel, dichloromethane:dichloromethane/ethanol 1:1)

Sources & evidence

ORD record
ord-bcad3e63fc834318b924259e691a10c8
Source dataset
uspto-grants-2013_09
Patent number
US08524724B2

Reaction notes

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