Phenyl 4-(carbamoylamino)-3-nitrobenzene-1-sulfonate → 5-Phenoxysulfonyl-2-ureidoaniline

HRID 2164409Notes

Reaction equation

HRID 2164409 reaction equation
[O:1]([S:8]([C:11]1[CH:12]=[CH:13][C:14]([NH:20][C:21]([NH2:23])=[O:22])=[C:15]([N+:17]([O-])=O)[CH:16]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO.COCCO.[Ni]>[O:1]([S:8]([C:11]1[CH:12]=[CH:13][C:14]([NH:20][C:21]([NH2:23])=[O:22])=[C:15]([CH:16]=1)[NH2:17])(=[O:9])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 15585382Phenyl 4-(carbamoylamino)-3-nitrobenzene-1-sulfonateHCID 178418361HCID 178418361, compound

Product 1

HCID 155855265-Phenoxysulfonyl-2-ureidoaniline

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 80192-MethoxyethanolSolvent

Procedure

33.7 g of 5-phenoxysulfonyl-2-ureidonitrobenzene in 250 ml of methanol and 250 ml of 2-methoxyethanol are hydrogenated under normal pressure with a catalytic amount of Raney nickel. After uptake of hydrogen is complete, the catalyst is filtered off with suction, washed with dimethylformamide and the solution is evaporated under reduced pressure, induced to crystallize with methanol, and the crystals are filtered off with suction and washed with methanol, melting point 180° C., decomposition.

Workup

  1. filtrationthe catalyst is filtered off with suction
  2. washwashed with dimethylformamide
  3. customthe solution is evaporated under reduced pressure
  4. customto crystallize with methanol
  5. filtrationthe crystals are filtered off with suction
  6. washwashed with methanol, melting point 180° C., decomposition.

Sources & evidence

ORD record
ord-71d78577a479446cb5eeb5b16ab49657
Source dataset
uspto-grants-1985_03
Patent number
US04504490

Reaction notes

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