2-Amino-2',5-dichlorobenzophenone → 2-[N-(4-Cyanophenylsulfonyl)amino]-2',5-dichlorobenzophenone

HRID 374631Notes

Reaction equation

HRID 374631 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Cl:12])=[O:5].[C:18]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)#[N:19]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:18]([C:20]1[CH:21]=[CH:22][C:23]([S:26]([NH:1][C:2]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:3]=2[C:4]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[Cl:12])=[O:5])(=[O:28])=[O:27])=[CH:24][CH:25]=1)#[N:19]

Participants

5

Reactant 2

HCID 180692-Amino-2',5-dichlorobenzophenoneHCID 394974-Cyanobenzenesulfonyl chloride

Product 1

HCID 233687202-[N-(4-Cyanophenylsulfonyl)amino]-2',5-dichlorobenzophenone

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

10 g of 2-amino-2',5-dichlorobenzophenone and 7.7 g of 4-cyanophenylsulfonyl chloride are heated in pyridine at 100° C. for 48 hours in the presence of 4.6 g of DMAP, the mixture is evaporated to dryness, water and ethyl acetate are added, the organic phase is washed with dilute hydrochloric water, water and an aqueous solution of sodium chloride and dried over magnesium sulfate and the solvent is evaporated off under vacuum. The precipitate formed is filtered off and then recrystallized twice from a DCM/isopropyl ether mixture to give the expected product.

Workup

  1. customthe mixture is evaporated to dryness, water and ethyl acetate
  2. additionare added
  3. washthe organic phase is washed
  4. additionwith dilute hydrochloric water, water
  5. dry with materialan aqueous solution of sodium chloride and dried over magnesium sulfate
  6. customthe solvent is evaporated off under vacuum
  7. customThe precipitate formed
  8. filtrationis filtered off
  9. customrecrystallized twice from a DCM/isopropyl ether mixture

Sources & evidence

ORD record
ord-47f7c9609c0b47858997b9c08e6665a8
Source dataset
uspto-grants-1996_01
Patent number
US05481005

Reaction notes

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