Diethylether ethylacetate → N-{2-[2-(4-Cyanophenyl)-ethyl]-1-(3,5-bis-trifluoromethyl-benzyl)-benzimidazol-5-yl}-benzenesulphonamide

HRID 840097Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([NH:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1.[C:34]([C:36]1[CH:41]=[CH:40][C:39]([CH:42]([CH3:46])C(O)=O)=[CH:38][CH:37]=1)#[N:35].[C:47](OCC)(=O)C.C(OCC)C>O=P(Cl)(Cl)Cl>[C:34]([C:36]1[CH:37]=[CH:38][C:39]([CH2:42][CH2:46][C:47]2[N:8]([CH2:9][C:10]3[CH:15]=[C:14]([C:16]([F:19])([F:17])[F:18])[CH:13]=[C:12]([C:20]([F:21])([F:22])[F:23])[CH:11]=3)[C:7]3[CH:6]=[CH:5][C:4]([NH:24][S:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)(=[O:26])=[O:27])=[CH:3][C:2]=3[N:1]=2)=[CH:40][CH:41]=1)#[N:35]

Participants

Conditions

Temperature: 110 °C

Procedure

N-{3-amino-4-(3,5-bis-trifluoromethyl-benzylamino)-phenyl}-benzenesulphonamide (5.5 g, 11.2 mmol) and p-cyano-phenylpropionic acid (2.35 g, 13.4 mmol) are taken up in 50 mL POCl3, and stirred for 2 h at 100-120° C. A precipitate settles out from the initially clear solution in the course of the reaction. After cooling it is diluted with 100 mL ethyl acetate/diethylether=1/1. The crystals are filtered off and washed with diethylether.

Workup

customA precipitate settles out from the initially clear solution in the course of the reaction
temperatureAfter cooling it
filtrationThe crystals are filtered off
washwashed with diethylether

Sources & evidence

ORD record: ord-400fab446fab43e59e69b90e0c6b442b
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06365584B1

Reaction notes

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