HCID 22502297, compound → 3,5-bis(methylsulfonyl)aniline

HRID 1814668Notes

Reaction equation

HRID 1814668 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[C:7]([S:14]([CH3:17])(=[O:16])=[O:15])[CH:6]=1)(=[O:4])=[O:3]>CO.[Pd]>[CH3:17][S:14]([C:7]1[CH:8]=[C:9]([NH2:11])[CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=1)(=[O:16])=[O:15]

Participants

4

Reactant 1

HCID 22502297HCID 22502297, compound

Product 1

HCID 7359073,5-bis(methylsulfonyl)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a slurry of 1,3-bis(methylsulfonyl)-5-nitrobenzene (0.7 g) in methanol (10 mL) was added palladium on charcoal (0.1 g) and the mixture was hydrogenated at atmospheric pressure and 25° C. for 1 hour. The reaction mixture was filtered and evaporated. The residue was suspended in ethyl acetate (25 mL) and HCl in ethyl acetate (5 mL, appr. 2M) was added. Filtration afforded the desired aniline as its hydrochloride salt, which was converted into an isocyanate using diphosgene as described previously.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. additionHCl in ethyl acetate (5 mL, appr. 2M) was added
  4. filtrationFiltration

Sources & evidence

ORD record
ord-72d20b77e97546aebd7f8ff9a1c48d5d
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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