O-Phenylenediamine → MLS003389252

HRID 600612Notes

Reaction equation

HRID 600612 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1>N1C=CC=CC=1.ClCCl>[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][S:15]([C:12]2[CH:13]=[CH:14][C:9]([CH3:19])=[CH:10][CH:11]=2)(=[O:17])=[O:16])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 7243O-PhenylenediamineHCID 73974-Toluenesulfonyl chloride

Product 1

HCID 256607MLS003389252Yield 95%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution in which 1,2-phenylenediamine (0.5 mmol) was dissolved in pyridine (1 mL) was added p-toluenesulfonyl chloride (1.1 mmol) at room temperature, and the mixture was reacted for 6 hours with stirring. After completion of the reaction, the reaction mixture was diluted with dichloromethane, and back extracted using 1N hydrochloric acid to remove pyridine. After the organic layer was dried with anhydrous sodium sulfate, and concentrated. The obtained solid was washed using diethyl ether on a Buchner funnel, and dried under reduced pressure to obtain an objective substance as a white solid in a yield of more than 95% yield.

Workup

  1. customthe mixture was reacted for 6 hours
  2. customAfter completion of the reaction
  3. extractionback extracted
  4. customto remove pyridine
  5. dry with materialAfter the organic layer was dried with anhydrous sodium sulfate
  6. concentrationconcentrated
  7. washThe obtained solid was washed
  8. customdried under reduced pressure
  9. customto obtain an objective substance as a white solid in a yield of more than 95% yield

Sources & evidence

ORD record
ord-182c00aece274692ad92990c9752b7d6
Source dataset
uspto-grants-2011_03
Patent number
US07902207B2

Reaction notes

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