Phosgene → rac-(4S*,5R*)-2-(5-tert-Butylsulfamoyl-4-chloro-2-ethoxyphenyl)-4,5-bis-(4-chlorophenyl)-4,5-dimethyl-4,5-dihydroimidazole-1-carbonyl chloride

HRID 2263928Notes

Reaction equation

HRID 2263928 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:39])[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[C:22]([O:36][CH2:37][CH3:38])=[CH:23][C:24]([Cl:35])=[C:25]([S:27]([NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:29])=[O:28])[CH:26]=3)=[N:9]2)=[CH:4][CH:3]=1.[C:40](Cl)([Cl:42])=[O:41]>C(N(CC)CC)C>[C:31]([NH:30][S:27]([C:25]1[C:24]([Cl:35])=[CH:23][C:22]([O:36][CH2:37][CH3:38])=[C:21]([C:10]2[N:9]([C:40]([Cl:42])=[O:41])[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)([CH3:39])[C:12]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)([CH3:13])[N:11]=2)[CH:26]=1)(=[O:29])=[O:28])([CH3:32])([CH3:33])[CH3:34]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 68683983rac-(4S*,5R*)-5-[4,5-Bis-(4-chlorophenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-N-tert-butyl-2-chloro-4-ethoxybenzenesulfonamide

Product 1

HCID 72455726rac-(4S*,5R*)-2-(5-tert-Butylsulfamoyl-4-chloro-2-ethoxyphenyl)-4,5-bis-(4-chlorophenyl)-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*)-5-[4,5-bis-(4-chlorophenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-N-tert-butyl-2-chloro-4-ethoxybenzene-sulfonamide (example 44) was reacted with phosgene in the presence of triethylamine to give the title compound.

Sources & evidence

ORD record
ord-01dc160ac0444f4c8c37b69ba0e1e951
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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