Sodium hydrogen sulfide hydrate → 3-(Methanesulfonyl)-5-nitroaniline

HRID 1957967Notes

Reaction equation

HRID 1957967 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)(=[O:4])=[O:3].O.S.[Na]>CO.C1(C)C=CC=CC=1>[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([CH:8]=[C:7]([N+:14]([O-:16])=[O:15])[CH:6]=1)[NH2:11])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 53442613Sodium hydrogen sulfide hydrate2×HCID 54402211HCID 54402211, compound

Product 1

HCID 673593153-(Methanesulfonyl)-5-nitroanilineYield 57%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of 1-(methylsulfonyl)-3,5-dinitro-benzene (1 g; 4 mmol) in methanol (80 ml) and toluene (20 ml) was treated with a solution of sodium hydrogensulfide-hydrate (227 mg; 4 mmol) in 20 ml methanol. The mixture was then refluxed for 3 hours additional 500 mg sodium hydrogensulfide-hydrate were added and refluxed for an additional hour. After cooling, the precipitate was filtrated and the filtrate concentrated. The residual was crystallized from methanol. 500 mg (2.31 mmol; 57% yield) of a yellow solid were obtained.

Workup

  1. additionwere added
  2. temperaturerefluxed for an additional hour
  3. temperatureAfter cooling
  4. filtrationthe precipitate was filtrated
  5. concentrationthe filtrate concentrated
  6. customThe residual was crystallized from methanol
  7. custom500 mg (2.31 mmol; 57% yield) of a yellow solid were obtained

Sources & evidence

ORD record
ord-5575453c701e46a189a39d26c0bbbcf0
Source dataset
uspto-grants-2013_04
Patent number
US08410100B2

Reaction notes

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