Phosgene → 4,5-Bis-(4-chloro-phenyl)-2-(4-ethoxy-2-methylsulfanyl-pyrimidin-5-yl)-4,5-dihydro-imidazole-1-carbonyl chloride

HRID 645737Notes

Reaction equation

HRID 645737 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[C:21]([O:28][CH2:29][CH3:30])=[N:22][C:23]([S:26][CH3:27])=[N:24][CH:25]=3)=[N:9]2)=[CH:4][CH:3]=1.[C:31](Cl)([Cl:33])=[O:32]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[N:11]([C:31]([Cl:33])=[O:32])[C:10]([C:20]3[C:21]([O:28][CH2:29][CH3:30])=[N:22][C:23]([S:26][CH3:27])=[N:24][CH:25]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6371PhosgeneHCID 866136294,5-bis-(4-chloro-phenyl)-2-(4-ethoxy-2-methylsulfanyl-pyrimidin-5-yl)-4,5-dihydro-1H-imidazole

Product 1

HCID 866136284,5-Bis-(4-chloro-phenyl)-2-(4-ethoxy-2-methylsulfanyl-pyrimidin-5-yl)-4,5-dihydro-imidazole-1-carbonyl chloride

Procedure

Using the procedure as described in example 1, cis-4-[4,5-bis-(4-chloro-phenyl)-2-(4-ethoxy-2-methylsulfanyl-pyrimidin-5-yl)-4,5-dihydro-1H-imidazole was reacted with phosgene to give cis-4-[4,5-bis-(4-chloro-phenyl)-2-(4-ethoxy-2-methylsulfanyl-pyrimidin-5-yl)-4,5-dihydro-imidazole-1-carbonyl chloride. The carbonyl chloride was then coupled with 2-piperazinone (Alfa) to give cis-4-[4,5-bis-(4-chloro-phenyl)-2-(4-ethoxy-2-methylsulfanyl-pyrimidin-5-yl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-2-one. HR-MS (ES, m/z) calculated for C27H27N6O3SCl2 [(M+H)+] 585.1237, observed 585.1236.

Sources & evidence

ORD record
ord-61564377de734a1aa15ddd83729de69b
Source dataset
uspto-grants-2010_04
Patent number
US07705007B2

Reaction notes

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