Triethylamine → N-benzenesulfonyl-3-(biphenyl-4-ylmethylamino)-4-butyrylaminobenzamide

HRID 1699622Notes

Reaction equation

HRID 1699622 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:12])[CH2:9][CH2:10][CH3:11].[C:14]1([S:20]([NH:23][C:24](=[O:46])[C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[C:27]([NH:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[CH:36][CH:35]=3)[CH:26]=2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C)C=O>[C:14]1([S:20]([NH:23][C:24](=[O:46])[C:25]2[CH:30]=[CH:29][C:28]([NH:31][C:8](=[O:12])[CH2:9][CH2:10][CH3:11])=[C:27]([NH:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)=[CH:36][CH:35]=3)[CH:26]=2)(=[O:21])=[O:22])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 53635937N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide

Product 1

HCID 18680826N-benzenesulfonyl-3-(biphenyl-4-ylmethylamino)-4-butyrylaminobenzamideYield 72.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (0.060 g) and butyryl chloride (0.084 g) are added to an N,N-dimethylformamide (2 ml) solution of N-benzenesulfonyl-4-amino-3-(biphenyl-4-ylmethylamino)benzamide (0.300 g). The solution is stirred for 1.5 hours at room temperature. The reaction solution is purified of itself using silica gel column chromatography Chloroform and N-benzenesulfonyl-3-(biphenyl-4-ylmethylamino)-4-butyrylaminobenzamide (0.250 g) is obtained. Methanol (5 ml) and 35% hydrochloric acid (0.50 g) are added to this and the solution is stirred for three hours at 60° C. The reaction is halted by adding 20% potassium bicarbonate. Extraction is performed with ethyl acetate and water. An organic layer is concentrated and the formed material is dissolved in a small amount of chloroform. By adding ether, crystallization is performed. The crystals are separated through filtration, dried and thus, 6-benzenesulfonyl-carbamoyl-1-(biphenyl-4-ylmethyl)-2-n-propylbenzimidazole Potassium Salt (0.157 g) is obtained. 1H-NMR (DMSO-d6, δ): 0.95 (3H, t, J=7.4 Hz), 1.77 (2H, q, J=7.5 Hz), 2.82 (2H, t, J=7.5 Hz), 5.55 (2H, s), 7.11 (2H, d, J=8.2 Hz), 7.32-7.38 (4H, m), 7.43 (2H, t, J=7.5 Hz), 7.47 (1H, d, J=8.4 Hz), 7.58-7.64 (4H, m), 7.79-7.83 (3H, m), 7.96 (1H, s).

Workup

  1. customThe reaction solution is purified of itself

Sources & evidence

ORD record
ord-0386844954b14beab08444ebacc3b6e3
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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