Water → HCID 54222598, compound

HRID 362894

Reaction equation

[C:1]1([C:7]2[N:8]=[CH:9][NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH2:21][CH2:22][Cl:23].O>CN(C=O)C>[Cl:23][CH2:22][CH2:21][N:8]1[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=[CH:9]1

Participants

Conditions

Temperature: 60 °C

Procedure

Step 1): A solution of 4,5-diphenylimidazole (2.5 g, 11.3 mmol) in dry DMF (20 ml) was added to a suspension of NaH (0.33 g, 13.8 mmol) in dry DMF (5 ml) at 50° C. under nitrogen atmosphere. The reaction mixture was heated at 60° C. for 2 hours. After heating, the mixture was added dropwise to a solution of 1-bromo-2-chloroethane (4.9 g, 33.9 mmol) in dry DMF (30 ml) over 1 hour at 50° C. The reaction mixture was heated continuously at 40° C. for 5 hours, then poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried (MgSO4) and concentrated. The precipitates were filtered off. The filtrate was concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate and hexane) to give 1-(2-chloroethyl)-4,5-diphenylimidazole (17.7%).

Workup

temperatureAfter heating
temperatureThe reaction mixture was heated continuously at 40° C. for 5 hours
extractionextracted with ethyl acetate
washThe organic layer was washed with water
dry with materialdried (MgSO4)
concentrationconcentrated
filtrationThe precipitates were filtered off
concentrationThe filtrate was concentrated
customThe residue was purified by column chromatography on silica gel (ethyl acetate and hexane)

Sources & evidence

ORD record: ord-558393d498c0477db34afe62487478cb
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05872115

Linked notes

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