Benzoyl chloride → N-benzenesulfonyl-4-benzoylamino-3-(biphenyl-4-ylmethylamino)benzamide

HRID 321974Notes

Reaction equation

HRID 321974 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:17]1([S:23]([NH:26][C:27](=[O:49])[C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[C:30]([NH:35][CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)=[CH:39][CH:38]=3)[CH:29]=2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)(O)[O-].[K+]>CN(C)C=O>[C:17]1([S:23]([NH:26][C:27](=[O:49])[C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:8](=[O:15])[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:30]([NH:35][CH2:36][C:37]3[CH:42]=[CH:41][C:40]([C:43]4[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=4)=[CH:39][CH:38]=3)[CH:29]=2)(=[O:24])=[O:25])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516893Potassium BicarbonateHCID 53635937N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide

Product 1

HCID 53867694N-benzenesulfonyl-4-benzoylamino-3-(biphenyl-4-ylmethylamino)benzamideYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.115 g) and benzoyl chloride (0.200 g) are added to an N,N-dimethylformamide (5 ml) solution of N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide (0.50 g). After stirring the solution for 15 hours at room temperature, a potassium bicarbonate aqueous solution is added to halt the reaction. Under reduced pressure, the solvent is removed. The residue is dissolved in a mixture of water and methanol, and its acidity is adjusted to pH 5˜6 with 10% hydrochloric acid. Precipitated crystals are collected, and dried. Preliminarily purified N-benzenesulfonyl-4-benzoylamino-3-(biphenyl-4-ylmethylamino)benzamide (0.393 g) is obtained, which is added to a mixture solvent of 10% hydrochloric acid (3.3 g), methanol (6 ml), and water (4 ml). Furthermore, 35% hydrochloric acid (0.5 g) is added and the solution is stirred for three hours at 60° C. After 20% potassium bicarbonate solution is added to turn the reaction solution into a basic, its acidity is adjusted to pH 5˜6 with 10% hydrochloric acid. Precipitated crystals are separated through filtration, dried and thus, 6-benzenesulfonylcarbamoyl-1-(biphenyl-4-ylmethyl)-2-phenylbenzimidazole (0.270 g) is obtained.

Workup

  1. customthe reaction
  2. customUnder reduced pressure, the solvent is removed
  3. dissolutionThe residue is dissolved in a mixture of water and methanol, and its acidity
  4. customPrecipitated crystals
  5. customare collected
  6. customdried

Sources & evidence

ORD record
ord-5374d75cca5041bb98efd05c51ec7f1e
Source dataset
uspto-grants-2001_04
Patent number
US06211177B1

Reaction notes

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