5-(3-Trifluoromethylphenylsulfonyloxy)-2-ureidonitrobenzene → 5-(3-Trifluoromethylphenylsulfonyloxy)-2-ureidoaniline

HRID 2164416Notes

Reaction equation

HRID 2164416 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([S:9]([O:12][C:13]2[CH:14]=[CH:15][C:16]([NH:22][C:23]([NH2:25])=[O:24])=[C:17]([N+:19]([O-])=O)[CH:18]=2)(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1.[H][H]>CO.COCCO.[Ni]>[F:26][C:2]([F:1])([F:27])[C:3]1[CH:4]=[C:5]([S:9]([O:12][C:13]2[CH:14]=[CH:15][C:16]([NH:22][C:23]([NH2:25])=[O:24])=[C:17]([CH:18]=2)[NH2:19])(=[O:11])=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 155854995-(3-Trifluoromethylphenylsulfonyloxy)-2-ureidonitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 155854705-(3-Trifluoromethylphenylsulfonyloxy)-2-ureidoaniline

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 80192-MethoxyethanolSolvent

Procedure

61.5 g of 5-(3-trifluoromethylphenylsulfonyloxy)-2-ureidonitrobenzene in 200 ml of methanol and 200 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 methanol and the solution is evaporated under reduced pressure, 1 liter of water is added, and the solid is filtered off with suction, washed with water and dried over NaOH, melting point 172° C., decomposition.

Workup

  1. filtrationthe catalyst is filtered off with suction
  2. washwashed with methanol
  3. customthe solution is evaporated under reduced pressure, 1 liter of water
  4. additionis added
  5. filtrationthe solid is filtered off with suction
  6. washwashed with water
  7. dry with materialdried over NaOH, melting point 172° C., decomposition.

Sources & evidence

ORD record
ord-1e69c5487f4b416b91c10fc3e96f5f82
Source dataset
uspto-grants-1985_03
Patent number
US04504490

Reaction notes

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