Methanesulfonyl chloride → 5-Cyano-7-(4-methanesulphonylmethylphenyl)-1-phenylbenzimidazole

HRID 644526Notes

Reaction equation

HRID 644526 reaction equation
[C:1]([C:3]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=2)[C:6]2[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#[N:2].C(N(C(C)C)CC)(C)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37].C(C1C=C(C2C=CC=C(CS(C)(=O)=O)C=2)C2N(C3C=CC=CC=3)C=NC=2C=1)#N>ClCCl>[C:1]([C:3]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][S:36]([CH3:35])(=[O:38])=[O:37])=[CH:20][CH:19]=2)[C:6]2[N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 674850065-Cyano-7-(4-hydroxymethylphenyl)-1-phenylbenzimidazoleHCID 674855565-Cyano-7-(3-methanesulphonylmethylphenyl)-1-phenylbenzimidazole

Product 1

HCID 674849905-Cyano-7-(4-methanesulphonylmethylphenyl)-1-phenylbenzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Cyano-7-(4-methanesulphonylmethylphenyl)-1-phenylbenzimidazole was prepared from 5-cyano-7-(4-hydroxymethylphenyl)-1-phenylbenzimidazole (500 mg, 1.54 mmol), diisopropylethylamine (0.82 ml, 4.62 mmol) and methanesulphonyl chloride (0.13 ml, 1.69 mmol) in dichloromethane (10 ml) using the method described for 5-cyano-7-(3-methanesulphonylmethylphenyl)-1-phenylbenzimidazole. The crude solution (approximately 0.14 M of product) was used directly in the next stage.

Sources & evidence

ORD record
ord-144dffb51cf049ce8c0b03d0764b78d2
Source dataset
uspto-grants-2010_04
Patent number
US07700638B2

Reaction notes

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