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

HRID 2263887Notes

Reaction equation

HRID 2263887 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:34])[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]=[CH:25][C:24]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:23][C:22]=3[O:31][CH2:32][CH3:33])=[N:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:42](Cl)([Cl:44])=[O:43]>ClCCl.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH3:34])[C:12]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)([CH3:13])[N:11]([C:42]([Cl:44])=[O:43])[C:10]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([CH3:28])([CH3:30])[CH3:29])=[CH:23][C:22]=3[O:31][CH2:32][CH3:33])=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 53628801rac-(4S*,5R*)-2-(4-tert-butyl-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazole

Product 1

HCID 72455721rac-(4S*,5R*)-4,5-bis(4-chlorophenyl)-2-(4-(tert-butyl)-2-ethoxy-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazole-1-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of rac-(4S*,5R*)-4,5-bis(4-chlorophenyl)-2-(4-(tert-butyl)-2-ethoxy-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazole (710 mg, 1.43 mmol, example 2) and triethylamine (400 uL, 2.86 mmol) in 12 mL of dichloromethane at 0° C. was added 1.13 mL of 1.9 M phosgene in toluene solution (Fluka). After stirring for 30 min the mixture was taken up in dichloromethane and washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by chromatography on silica gel, eluting with hexane-ethyl acetate (4:1) provided 689 mg of rac-(4S*,5R*)-4,5-bis(4-chlorophenyl)-2-(4-(tert-butyl)-2-ethoxy-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazole-1-carbonyl chloride as a white solid.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by chromatography on silica gel
  6. washeluting with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-ec9f5141331b47fba90be8bd03f31853
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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