Triethylamine → 4-(Phenylsulfamoyl)phenyl 4-(2-bromoethyl)benzoate

HRID 904928Notes

Reaction equation

HRID 904928 reaction equation
[C:1]1([NH:7][S:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Br:25][CH2:26][CH2:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1>C(Cl)Cl>[Br:25][CH2:26][CH2:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([O:17][C:14]2[CH:13]=[CH:12][C:11]([S:8](=[O:9])(=[O:10])[NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:16][CH:15]=2)=[O:33])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 99212394-hydroxy-N-phenylbenzenesulfonamideHCID 140920984-(2-Bromoethyl)benzoyl chloride

Product 1

HCID 204418094-(Phenylsulfamoyl)phenyl 4-(2-bromoethyl)benzoateYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of 24.93 g (0.10 mol) of N-phenyl-4-hydroxybenzenesulfonamide, 10.12 g (0.10 mol) of triethylamine and 150 ml of methylene chloride was added, dropwise, a solution of 24.75 g (0.10 mol) of 4-(2-bromoethyl)benzoyl chloride in 150 ml of methylene chloride over a period of 12 minutes. The reaction mixture was stirred at room temperature for 3 hours, after which 500 ml of methylene chloride were added. The solution was washed once with 2% HCl and twice with water, dried over magnesium sulfate and concentrated to a white solid. Recrystallization from ethanol gave 39.7 g (86.1% of theory) of 4-(N-phenylsulfamoyl)phenyl 4-(2-bromoethyl)benzoate, mp=156°-7° C.

Workup

  1. additionwas added
  2. washThe solution was washed once with 2% HCl and twice with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to a white solid
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-f8f68397a7be45b4996ada6d610e9266
Source dataset
uspto-grants-1983_12
Patent number
US04420630

Reaction notes

Loading…