2-(3-Acetylureido)-5-phenoxysulfonylnitrobenzene → 2-(3-Acetylureido)-5-phenoxysulfonylaniline

HRID 2164412Notes

Reaction equation

HRID 2164412 reaction equation
[C:1]([NH:4][C:5](=[O:26])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:15])=[O:14])=[CH:9][C:8]=1[N+:23]([O-])=O)(=[O:3])[CH3:2].[H][H]>CO.COCCO.[Ni]>[C:1]([NH:4][C:5](=[O:26])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:15])=[O:14])=[CH:9][C:8]=1[NH2:23])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 155853832-(3-Acetylureido)-5-phenoxysulfonylnitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 155853842-(3-Acetylureido)-5-phenoxysulfonylaniline

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 80192-MethoxyethanolSolvent

Procedure

48 g of 2-(3-acetylureido)-5-phenoxysulfonylnitrobenzene in 300 ml of methanol and 300 ml of 2-methoxyethanol are hydrogenated under normal pressure with a catalytic amount of Raney nickel. After hydrogen uptake is complete, the catalyst is filtered off with suction, washed with dimethylformamide and the solution is evaporated under reduced pressure. The residue is stirred with hot methanol, and the solid is filtered off cold under suction and washed with methanol and diisopropyl ether, melting point 202° C., decomposition.

Workup

  1. filtrationthe catalyst is filtered off with suction
  2. washwashed with dimethylformamide
  3. customthe solution is evaporated under reduced pressure
  4. filtrationthe solid is filtered off cold under suction
  5. washwashed with methanol and diisopropyl ether, melting point 202° C., decomposition.

Sources & evidence

ORD record
ord-dafcb30e17ad4cb490116da48625e467
Source dataset
uspto-grants-1985_03
Patent number
US04504490

Reaction notes

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