4-Bromoaniline → N-(4-Bromophenyl)-4-[(propane-2-sulfonyl)amino]benzamide

HRID 1982278Notes

Reaction equation

HRID 1982278 reaction equation
[CH:1]([S:4]([NH:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:12](=[O:13])[C:11]2[CH:15]=[CH:16][C:8]([NH:7][S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])=[CH:9][CH:10]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 78074-BromoanilineHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 134899814-[(Propane-2-sulfonyl)amino]benzoyl chloride

Product 1

HCID 13489982N-(4-Bromophenyl)-4-[(propane-2-sulfonyl)amino]benzamideYield 52.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 250 mg of 4-isopropanesulfonamidobenzoylchloride 1, 181 mg of 4-bromoaniline 2, 106 mg of triethylamine, and 5 ml of methylene chloride is stirred at room temperature for 5 minutes. The reaction mixture is neutralized with a sodium bicarbonate solution, and extracted with methylene chloride. The organic layer is concentrated under reduced pressure, and the residue is chromatographed on a column of silica-gel. The eluate with 3% methanolmethylene chloride is concentrated, and the residue is crystallized from ethyl acetate-isopropyl ether. The crude resulting crystals are recrystallized from ethyl acetateisopropyl ether to give 200 mg of 4'-bromo-4-isopropanesulfonamidobenzanilide 3 as pure specimen, m.p. 213°-214° C.

Workup

  1. extractionextracted with methylene chloride
  2. concentrationThe organic layer is concentrated under reduced pressure
  3. customthe residue is chromatographed on a column of silica-gel
  4. concentrationThe eluate with 3% methanolmethylene chloride is concentrated
  5. customthe residue is crystallized from ethyl acetate-isopropyl ether
  6. customThe crude resulting crystals
  7. customare recrystallized from ethyl acetateisopropyl ether

Sources & evidence

ORD record
ord-b2d4a1026a424abfac07f803ca26f855
Source dataset
uspto-grants-1986_06
Patent number
US04595780

Reaction notes

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