4-Nitrobenzenesulfonyl chloride → 5-Chloro-2'-fluoro-2-[(4-nitrophenylsulfonyl)amino]benzophenone

HRID 374626Notes

Reaction equation

HRID 374626 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[F:12])=[O:5].[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)([O-:20])=[O:19]>N1C=CC=CC=1>[Cl:17][C:14]1[CH:15]=[CH:16][C:2]([NH:1][S:27]([C:24]2[CH:23]=[CH:22][C:21]([N+:18]([O-:20])=[O:19])=[CH:26][CH:25]=2)(=[O:28])=[O:29])=[C:3]([CH:13]=1)[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])=[O:5]

Participants

4

Reactant 2

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 699122-Amino-5-chloro-2'-fluorobenzophenone

Product 1

HCID 104106845-Chloro-2'-fluoro-2-[(4-nitrophenylsulfonyl)amino]benzophenone

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture containing 24.9 g of 2-amino-5-chloro-2'-fluorobenzophenone and 22.1 g of 4-nitrophenylsulfonyl chloride is refluxed for 10 hours in pyridine. It is evaporated to dryness, water and ethyl acetate are then added and the ethyl acetate phase is washed with water and an aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated under vacuum. The expected product precipitates on evaporation; it is filtered off and recrystallized from a DCM/isopropyl ether mixture to give 20 g.

Workup

  1. customIt is evaporated to dryness, water and ethyl acetate
  2. additionare then added
  3. washthe ethyl acetate phase is washed with water
  4. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulfate
  5. customevaporated under vacuum
  6. customThe expected product precipitates on evaporation
  7. filtrationit is filtered off
  8. customrecrystallized from a DCM/isopropyl ether mixture
  9. customto give 20 g

Sources & evidence

ORD record
ord-f5a10398d4ce4cd58693002033b11ffc
Source dataset
uspto-grants-1996_01
Patent number
US05481005

Reaction notes

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