Phosgene → rac-(4S*,5R*)-2-(4-tert-butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4-ethyl-4,5-dihydro-imidazole-1-carbonyl chloride

HRID 2264077Notes

Reaction equation

HRID 2264077 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:20])[C:9]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)([NH2:12])[CH2:10][CH3:11])=[CH:4][CH:3]=1.[CH:21]([O:24][C:25]1[CH:34]=[C:33](OC)[CH:32]=[CH:31][C:26]=1[C:27](OC)=O)([CH3:23])C.C[Al](C)C.[C:41]([Cl:44])(Cl)=[O:42]>C(N(CC)CC)C>[C:5]([C:33]1[CH:32]=[CH:31][C:26]([C:27]2[NH:20][CH:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:9]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)([CH2:10][CH3:11])[N:12]=2)=[C:25]([O:24][CH2:21][CH3:23])[CH:34]=1)([CH3:8])([CH3:6])[CH3:4].[C:5]([C:33]1[CH:32]=[CH:31][C:26]([C:27]2[N:20]([C:41]([Cl:44])=[O:42])[CH:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:9]([C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)([CH2:10][CH3:11])[N:12]=2)=[C:25]([O:24][CH2:21][CH3:23])[CH:34]=1)([CH3:8])([CH3:6])[CH3:4]

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 14276512Methyl 2-isopropoxy-4-methoxybenzoateHCID 16682925TrimethylaluminumHCID 68684718rac-(1R*,2S*)-1,2-bis-(4-chloro-phenyl)-butane-1,2-diamine

Product 2

HCID 53628804rac-(4S*,5R*)-2-(4-tert-butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4-ethyl-4,5-dihydro-imidazole-1-carbonyl chlorideHCID 178466276HCID 178466276, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

rac-(4S*,5R*)-2-(4-tert-butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4-ethyl-4,5-dihydro-1H-imidazole was prepared from rac-(1R*,2S*)-1,2-bis-(4-chloro-phenyl)-butane-1,2-diamine (prepared from 3,4-bis-aryl-1,2,5-thiadiazole-1,1-dioxide and ethylmagnesium bromide as described in example 170) and methyl 2-isopropoxy-4-methoxy-benzoate in the presence of trimethylaluminum using the procedure as described in example 2. It was then reacted with phosgene in the presence of triethylamine to give rac-(4S*,5R*)-2-(4-tert-butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4-ethyl-4,5-dihydro-imidazole-1-carbonyl chloride.

Sources & evidence

ORD record
ord-8e0223c32fb34998bb8f3e636cb700ba
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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