Imidazole → HCID 18434133, compound

HRID 1636740Notes

Reaction equation

[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Br[CH2:9]/[CH:10]=[CH:11]/[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=2)=[O:21])=[CH:16][CH:15]=1.O>CN(C=O)C>[Br:28][C:25]1[CH:24]=[CH:23][C:22]([C:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:12]/[CH:11]=[CH:10]/[CH2:9][N:1]3[CH:5]=[CH:4][N:3]=[CH:2]3)=[CH:15][CH:16]=2)=[O:21])=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 68 mg of imidazole in 4 ml of DMF is added dropwise to a suspension of 44 mg of 55% sodium hydride in 4 ml of DMF. After heating the mixture to 70° C. a solution of 441 mg of (E)-[4-(4-bromo-but-2-enyloxy)-phenyl]-(4-bromo-phenyl)-methanone in 12 ml of DMF is added dropwise. Then, the mixture is stirred at 70° C. for a further 1 h. and, after cooling, poured into 5 ml of water and concentrated. The residue is treated with water and extracted with methylene chloride. The organic phases are washed with saturated sodium chloride solution, dried and evaporated. The residue is purified on silica gel with toluene/acetone/triethylamine (70:29:1). The (E)-(4-bromo-phenyl)-[4-(4-imidazol-1-yl-but-2-enyloxy)-phenyl]-methanone (140 mg) is obtained as the beige solid base which is converted into the hydrochloride, MS: m/e 397 (M, 1Br).

Workup

additionis added dropwise
temperatureafter cooling
concentrationconcentrated
additionThe residue is treated with water
extractionextracted with methylene chloride
washThe organic phases are washed with saturated sodium chloride solution
customdried
customevaporated
customThe residue is purified on silica gel with toluene/acetone/triethylamine (70:29:1)

Sources & evidence

ORD record: ord-2e6cd641b4de44c3bd7222794810fd4b
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06034275

Reaction notes

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