Phosgene → rac-(4S*,5R*)-4,5-Bis-(4-chlorophenyl)-2-[2-ethoxy-4-methoxy-5-(pyrrolidine-1-sulfonyl)-phenyl]-4,5-dimethyl-4,5-dihydroimidazole-1-carbonyl chloride

HRID 2263941Notes

Reaction equation

HRID 2263941 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:40])[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)([CH3:13])[NH:11][C:10]([C:21]3[CH:26]=[C:25]([S:27]([N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)(=[O:29])=[O:28])[C:24]([O:35][CH3:36])=[CH:23][C:22]=3[O:37][CH2:38][CH3:39])=[N:9]2)=[CH:4][CH:3]=1.[C:41](Cl)([Cl:43])=[O:42]>C(N(CC)CC)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:40])[C:12]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)([CH3:13])[N:11]([C:41]([Cl:43])=[O:42])[C:10]([C:21]3[CH:26]=[C:25]([S:27]([N:30]4[CH2:31][CH2:32][CH2:33][CH2:34]4)(=[O:28])=[O:29])[C:24]([O:35][CH3:36])=[CH:23][C:22]=3[O:37][CH2:38][CH3:39])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 68687383rac-(4S*,5R*)-4,5-bis-(4-chlorophenyl)-2-[2-ethoxy-4-methoxy-5-(pyrrolidine-1-sulfonyl)phenyl]-4,5-dimethyl-4,5-dihydro-1H-imidazole

Product 1

HCID 72455718rac-(4S*,5R*)-4,5-Bis-(4-chlorophenyl)-2-[2-ethoxy-4-methoxy-5-(pyrrolidine-1-sulfonyl)-phenyl]-4,5-dimethyl-4,5-dihydroimidazole-1-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a manner analogous to the method described in example 3, rac-(4S*,5R*)-4,5-bis-(4-chlorophenyl)-2-[2-ethoxy-4-methoxy-5-(pyrrolidine-1-sulfonyl)phenyl]-4,5-dimethyl-4,5-dihydro-1H-imidazole was reacted with phosgene in the presence of triethylamine to give the title compound.

Sources & evidence

ORD record
ord-4e4bb8a430824123bd5efcc8c86d96fc
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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