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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2264077Generated: October 26, 2026

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

https://huagongshe.com/reaction/2264077

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPhosgeneHCID 6371—
ReactantMethyl 2-isopropoxy-4-methoxybenzoateHCID 14276512—
ReactantTrimethylaluminumHCID 16682925—
Reactantrac-(1R*,2S*)-1,2-bis-(4-chloro-phenyl)-butane-1,2-diamineHCID 68684718—
SolventTriethylamineHCID 8471—
Productrac-(4S*,5R*)-2-(4-tert-butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4-ethyl-4,5-dihydro-imidazole-1-carbonyl chlorideHCID 53628804—
ProductHCID 178466276HCID 178466276—

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07851626B2
Source datasetuspto-grants-2010_12
ORD IDord-8e0223c32fb34998bb8f3e636cb700ba
Source noteuspto-grants-2010_12