Hydrochloric Acid → (4-aminophenyl)-N-methylmethylenesulfonamide hydrochloride

HRID 1194753Notes

Reaction equation

HRID 1194753 reaction equation
[CH3:1][NH:2][S:3]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][CH:8]=1)(=[O:5])=[O:4].[H][H].[ClH:18]>C(O)C.O.[Pd]=O>[ClH:18].[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][S:3]([NH:2][CH3:1])(=[O:5])=[O:4])=[CH:8][CH:9]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 703312N-Methyl-1-(4-nitrophenyl)methanesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 14234262(4-aminophenyl)-N-methylmethylenesulfonamide hydrochloride

Reagents, catalysts & solvents 3

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of N-methyl-4-nitrobenzenemethanesulphonamide (30 g) in ethanol (150 ml), water (300 ml) and hydrochloric acid (2N, 65 ml) was hydrogenated over 10% palladium oxide on charcoal (7.5 g, 50% paste with water) until hydrogen uptake ceased (9.75 l). The catalyst was removed by filtration through "hyflo" and the filter pad was washed with water (30 ml). The filtrate was evaporated under reduced pressure to give the title compound as a pale yellow powder (28.2 g) m.p. 143°-144° C.

Workup

  1. customThe catalyst was removed by filtration through "hyflo"
  2. washthe filter pad was washed with water (30 ml)
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ccdbfabfb80947ddaf33b139441bf3e6
Source dataset
uspto-grants-1989_03
Patent number
US04816470

Reaction notes

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