Phosgene → HCID 86612880, compound

HRID 2263952Notes

Reaction equation

HRID 2263952 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([CH3:32])[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:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][C:22]=3[O:29][CH2:30][CH3:31])=[N:9]2)=[CH:4][CH:3]=1.[C:33](Cl)([Cl:35])=[O:34].C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH3:32])[C:12]([C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)([CH3:13])[N:11]([C:33]([Cl:35])=[O:34])[C:10]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][C:22]=3[O:29][CH2:30][CH3:31])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6371Phosgene2×HCID 8471Triethylamine2×HCID 17754545HCID 17754545, compound

Product 1

HCID 86612880HCID 86612880, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of rac-4-[(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl]-3-ethoxy-benzonitrile (190 mg, 0.31 mmol) in dichloromethane was cooled to 0° C. and treated with phosgene (2.5 mL, 0.47 mmol, 1.9 M in toluene) and triethylamine (0.66 g, 0.65 mmol). After 1 h, the reaction was charged with the same quantities of phosgene and triethylamine. After an additional 1 h at 0° C., the reaction was worked up in ice water and dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated to give an oil. It was purified by a short plug of silica gel (eluting with 20% ethyl acetate/hexane) to give rac-(4S*,5R*)-4,5-bis-(4-chloro-phenyl)-2-(4-cyano-2-ethoxy-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride.

Workup

  1. waitAfter an additional 1 h at 0° C.
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give an oil
  6. customIt was purified by a short plug of silica gel (eluting with 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8486e748c30c49e18001fa2311832354
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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