HCID 18680985, compound → HCID 18681138, compound

HRID 276009Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([CH2:12][CH2:13][CH3:14])[N:9]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:8]=2[CH:23]=1)(=O)[NH2:2]>ClCCl.C(N(CC)CC)C.O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl>[Cl:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][N:9]1[C:8]2[CH:23]=[C:4]([C:1]#[N:2])[CH:5]=[CH:6][C:7]=2[N:11]=[C:10]1[CH2:12][CH2:13][CH3:14]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 1 mol of titanium tetrachloride in 0.14 ml of dichloromethane and 0.36 ml of triethylamine were added to a solution of 200 mg of 6-carbamoyl-1-(2-chlorobenzyl)-2-n-propylbenzimidazole in 4 ml of tetrahydrofuran at 0° C., and the mixture was stirred at 20° C. for 2 hours. The reaction mixture was separated with ethyl acetate and with water. The organic layer was washed with water, dried, and then concentrated under reduced pressure. The residue was developed and purified through column chromatography using a mixture of ethyl acetate and hexane (at a ratio of from 1:10 to 1:3), and was further recrystallized from a mixture of ethyl acetate and hexane to give 140 mg of 1-(2-chlorobenzyl)-6-cyano-2-n-propylbenzimidazole (87).

Workup

customThe reaction mixture was separated with ethyl acetate and with water
washThe organic layer was washed with water
customdried
concentrationconcentrated under reduced pressure
custompurified through column chromatography
additiona mixture of ethyl acetate and hexane (at a ratio of from 1:10 to 1:3), and
customwas further recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-62e0f638b25441ddb97734d97f88fc58
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06352985B1

Reaction notes

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