4-Chlorobenzenesulfonyl chloride → HCID 9959089, compound

HRID 990107Notes

Reaction equation

HRID 990107 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[C:10]2[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:11]=2[NH2:17])=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1>C(Cl)Cl>[Br:16][C:14]1[CH:13]=[CH:12][C:11]([NH:17][S:26]([C:23]2[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=2)(=[O:28])=[O:27])=[C:10]([CH:15]=1)[C:9]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)=[O:18]

Participants

4

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 18419745HCID 18419745, compound

Product 1

HCID 9959089HCID 9959089, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(4-Bromophenyl)-2-amino-5-bromobenzamide (8.64 g, 23.3 mmol), 4-chlorobenzenesulfonyl chloride (4.98 g, 23.6 mmol), and 7.37 g (93.2 mmol) in 300 ml of CH2Cl2 was allowed to stand at room temperature for 2 days. The reaction mixture was concentrated under vacuum and the residue dissolved in EtOAc. The solution was washed twice with 10% HCl, water, 5% NaHCO3, water, and dried over MgSO4. Concentration and recrystallization from 10% EtOAc in hexane gave product which had satisfactory NMR, MS, and elemental analysis.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe solution was washed twice with 10% HCl, water, 5% NaHCO3, water
  4. dry with materialdried over MgSO4
  5. concentrationConcentration and recrystallization from 10% EtOAc in hexane
  6. customgave product which

Sources & evidence

ORD record
ord-928787e5fb8545f79d107e51c8159aa7
Source dataset
uspto-grants-2002_10
Patent number
US06458845B1

Reaction notes

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