Phosgene → cis-4,5-Bis-(4-chloro-phenyl)-2-[4-(1-diethylcarbamoyl-1-methyl-ethyl)-2-ethoxy-phenyl]-4,5-dihydro-imidazole-1-carbonyl chloride

HRID 2425724Notes

Reaction equation

HRID 2425724 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[NH:11][C:10]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([CH3:35])([CH3:34])[C:27]([N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])=[O:28])=[CH:22][C:21]=3[O:36][CH2:37][CH3:38])=[N:9]2)=[CH:4][CH:3]=1.[C:39](Cl)([Cl:41])=[O:40]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:12]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[N:11]([C:39]([Cl:41])=[O:40])[C:10]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([C:27](=[O:28])[N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])([CH3:35])[CH3:34])=[CH:22][C:21]=3[O:36][CH2:37][CH3:38])=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6371PhosgeneHCID 672468402-{4-[4,5-Bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazol-2-yl]-3-ethoxy-phenyl}-N,N-diethyl-isobutyramide

Product 1

HCID 86602333cis-4,5-Bis-(4-chloro-phenyl)-2-[4-(1-diethylcarbamoyl-1-methyl-ethyl)-2-ethoxy-phenyl]-4,5-dihydro-imidazole-1-carbonyl chlorideYield 56%

Procedure

2-{4-[4,5-Bis-(4-chloro-phenyl)-4,5-dihydro-1H-imidazol-2-yl]-3-ethoxy-phenyl}-N,N-diethyl-isobutyramide (90 mg, 0.163 mmol) was reacted with phosgene (101 uL, 0.196 mmol, 20% solution in toluene) using the procedure as described in example 12 to give cis-4,5-bis-(4-chloro-phenyl)-2-[4-(1-diethylcarbamoyl-1-methyl-ethyl)-2-ethoxy-phenyl]-4,5-dihydro-imidazole-1-carbonyl chloride (56 mg, 56% yield) as white solids.

Sources & evidence

ORD record
ord-cc965209390e4b1f9dd935286475dfe6
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

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