Chloroacetyl chloride → HCID 12016812, compound

HRID 431074Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([NH:21][CH2:22][C:23]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH:26]=[CH:25][CH:24]=4)=[CH:20][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)#[N:2].CN1CCOCC1.[Cl:40][CH2:41][C:42](Cl)=[O:43]>ClCCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][C:11]2[N:15]([CH3:16])[C:14]3[CH:17]=[CH:18][C:19]([N:21]([CH2:22][C:23]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[CH:26]=[CH:25][CH:24]=4)[C:42](=[O:43])[CH2:41][Cl:40])=[CH:20][C:13]=3[N:12]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

Conditions

Temperature: 10 °C

Procedure

A mixture of 4.0 g (9.6 mmol) of 2-[2-(4-cyanophenyl)-ethyl]-1-methyl-5-naphth-1-ylmethylamino-benzimidazole and 1.1 mL (10.0 mmol) of N-methylmorpholine in 80 ml of dichloromethane was cooled to 10° C. A solution of 0.8 mL (10.0 mmol) of chloroacetylchloride in 15 ml of dichloromethane was added dropwise to the solution within 15 min. The mixture was then stirred for 30 min at ambient temperature. It was washed with water and dilute potassium carbonate solution, dried and concentrated by evaporation. The product is chromatographed on silica gel.

Workup

washIt was washed with water and dilute potassium carbonate solution
customdried
concentrationconcentrated by evaporation
customThe product is chromatographed on silica gel

Sources & evidence

ORD record: ord-72cca27b16604b7e941c386731d7d35d
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06656956B2

Reaction notes

Loading…