HCID 14555110, compound → HCID 13286115, compound

HRID 1194763Notes

Reaction equation

HRID 1194763 reaction equation
[CH2:1]([NH:3][S:4]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)(=[O:6])=[O:5])[CH3:2].[H][H]>C(O)C.[Pd]=O>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][S:4]([NH:3][CH2:1][CH3:2])(=[O:6])=[O:5])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 14555110HCID 14555110, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13286115HCID 13286115, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 5083724Palladium monoxideCatalystHCID 702EthanolSolvent2×

Procedure

A solution of N-ethyl-4-nitrobenzenemethanesulphonamide (4.35 g) in warm ethanol (125 ml) was added to 10% palladium oxide on carbon (0.75 g, 50% aqueous paste) prereduced in ethanol (25 ml) and hydrogenated at atmospheric pressure. Hydrogen uptake (1400 ml) ceased after 20 minutes. The suspension was filtered and the catalyst was washed with methanol (100 ml) and ethanol (100 ml). Evaporation of the combined filtrate and washings produced a grey solid (2.0 g) which was crystallised from isoprpopanol (120 ml) to present the title compound as cream micro needles (1.48 g), m.p. 161°-164°.

Workup

  1. filtrationThe suspension was filtered
  2. washthe catalyst was washed with methanol (100 ml) and ethanol (100 ml)
  3. customEvaporation of the combined filtrate and washings

Sources & evidence

ORD record
ord-cb8541f4937248f7ae6eb147d5eb3cc5
Source dataset
uspto-grants-1989_03
Patent number
US04816470

Reaction notes

Loading…