P-Phenylenediamine → HCID 13628653, compound

HRID 981811Notes

Reaction equation

HRID 981811 reaction equation
[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1Cl)(=[O:6])=[O:5].[C:17]1([NH2:24])[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1>CO>[OH:1][CH2:2][CH2:3][S:4]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[NH:23][C:20]1[CH:21]=[CH:22][C:17]([NH2:24])=[CH:18][CH:19]=1)(=[O:6])=[O:5]

Participants

4

Reactant 2

HCID 7814P-PhenylenediamineHCID 136286432-Chloro-5-nitrophenyl hydroxyethyl sulfone

Product 1

HCID 13628653HCID 13628653, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

132.85 g of 2-chloro-5-nitrophenyl hydroxyethyl sulfone are added at 65° C. under nitrogen to a solution of 118.8 g of 1,4-phenylenediamine in 500 ml of methanol in the course of 30 minutes. The reaction solution is stirred at this temperature for a further 4 hours and is then allowed to cool down to room temperature, and the reaction product is crystallized by addition of 1 l of ice-water. Filtering with suction and drying gives 168 g of 2-(4-aminophenylamino)-5-nitrophenyl hydroxyethyl sulfone having a melting point of 147°-149° C. and a purity of >99%, which corresponds to a yield of 99% of theory, relative to starting 2-chloro-5-nitrophenyl hydroxyethyl sulfone.

Workup

  1. customthe reaction product is crystallized by addition of 1 l of ice-water
  2. filtrationFiltering with suction
  3. customdrying

Sources & evidence

ORD record
ord-5ca6980a66f3453ea3e81da48363537e
Source dataset
uspto-grants-1991_02
Patent number
US04992589

Reaction notes

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