Methyl isothiocyanate → 4-[4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazine-1-carbothioic acid methylamide

HRID 31518Notes

Reaction equation

HRID 31518 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[N:12]([C:21]([N:23]3[CH2:28][CH2:27][N:26](CCC#N)[CH2:25][CH2:24]3)=[O:22])[C:11]([C:33]3[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][C:34]=3[O:43][CH2:44][CH3:45])=[N:10]2)=[CH:5][CH:4]=1.[CH3:46][N:47]=[C:48]=[S:49]>C(Cl)Cl>[CH3:46][NH:47][C:48]([N:26]1[CH2:27][CH2:28][N:23]([C:21]([N:12]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH:9]([C:6]3[CH:5]=[CH:4][C:3]([Cl:2])=[CH:8][CH:7]=3)[N:10]=[C:11]2[C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][C:34]=2[O:43][CH2:44][CH3:45])=[O:22])[CH2:24][CH2:25]1)=[S:49]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 111814993-{4-[4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazin-1-yl}-propionitrile hydrochloride

Product 1

HCID 112508864-[4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazine-1-carbothioic acid methylamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[4,5-Bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazol-1-yl]-piperazin-1-yl-methanone (279 mg, 0.47 mmol, example 8A) was dissolved in methylene chloride (3 mL) and methylisothiocyanate (64 uL) was added. After stirring 3 h, the reaction mixture was concentrated to dryness. Purification of the crude residue by flash chromatography (silica gel) eluting with ethyl acetate and hexanes gave 4-[4,5-bis-(4-chloro-phenyl)-2-(2-ethoxy-4-trifluoromethyl-phenyl)-4,5-dihydro-imidazole-1-carbonyl]-piperazine-1-carbothioic acid methylamide (195 mg). LR-MS: 664.4 [(M+H)+].

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. customPurification of the crude residue by flash chromatography (silica gel)
  3. washeluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-3897b0b2dfad4860b8cc00f2933b7140
Source dataset
uspto-grants-2008_09
Patent number
US07425638B2

Reaction notes

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