O-Phenylenediamine → HCID 15481004, compound

HRID 486608Notes

Reaction equation

HRID 486608 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(N(CC)CC)C>O1CCOCC1>[NH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH:8][S:17]([C:14]1[CH:13]=[CH:12][C:11]([O:10][CH3:9])=[CH:16][CH:15]=1)(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 74014-Methoxybenzenesulfonyl chlorideHCID 8471Triethylamine

Product 1

HCID 15481004HCID 15481004, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

33.1 g (0.3 mol) of 1,2-phenylenediamine was dissolved in 200 ml of dioxane. A solution of 20.87 g (0.1 mol) of 4-methoxybenzenesulfonyl chloride in 110 ml of dioxane was added thereto under stirring. The resulting mixture was stirred at room temperature overnight. 12.1 g (0.12 mol) of triethylamine was added thereto. After concentration followed by addition of an aqueous citric acid solution and ethyl acetate, the organic layer was separated, concentrated and purified by silica gel column chromatography to obtain 27.1 g of the title compound.

Workup

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. concentrationAfter concentration
  3. additionfollowed by addition of an aqueous citric acid solution and ethyl acetate
  4. customthe organic layer was separated
  5. concentrationconcentrated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-87965d0fc6cf4b13b5477d23a5962eb6
Source dataset
uspto-grants-1994_03
Patent number
US05292758

Reaction notes

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