Potassium Carbonate → HCID 13489983, compound

HRID 1982281Notes

Reaction equation

HRID 1982281 reaction equation
[Br:1][C:2]1[CH:23]=[CH:22][C:5]([NH:6][C:7](=[O:21])[C:8]2[CH:13]=[CH:12][C:11]([NH:14][S:15]([N:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:31]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:33](=[O:34])[O:32]1>CC(C)=O>[Br:1][C:2]1[CH:23]=[CH:22][C:5]([NH:6][C:7](=[O:21])[C:8]2[CH:9]=[CH:10][C:11]([N:14]([S:15]([N:18]([CH3:20])[CH3:19])(=[O:16])=[O:17])[CH:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:33](=[O:34])[O:32]3)=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 13321993N-(4-Bromophenyl)-4-[(dimethylsulfamoyl)amino]benzamide

Product 1

HCID 13489983HCID 13489983, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1.0 g of 4'-bromo-4-[(dimethylaminosulfonyl)amino]benzanilide 10 and 10 ml of dried acetone are added 416 mg of potassium carbonate powder and 642 mg of 3-bromophthalide 11, and the mixture is refluxed for 1 hour. The reaction mixture is concentrated; to the residue is added water, and the precipitating crystals are collected by filtration and recrystallized from acetonitrile to give 680 mg of 4'-bromo-4-[(dimethylaminosulfonyl)(3-phthalidyl)amino]benzanilide 12 as crystals, m.p. 244°-245.5° C.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. concentrationThe reaction mixture is concentrated
  3. additionto the residue is added water
  4. filtrationthe precipitating crystals are collected by filtration
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-77e0831413064f8585a44a85004a737a
Source dataset
uspto-grants-1986_06
Patent number
US04595780

Reaction notes

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