Hexyl isocyanate → N-(Hexyl)-4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-1-methylimidazole-2-carboxamide

HRID 2101721Notes

Reaction equation

[CH2:1]([N:7]=[C:8]=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]=[CH:19][N:20]([CH3:30])[C:21]=2[C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])=[CH:13][CH:12]=1>>[CH2:1]([NH:7][C:8]([C:19]1[N:20]([CH3:30])[C:21]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=2)[N:18]=1)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Reactant 2

HCID 75659Hexyl isocyanate

HCID 220660834-(4-Chlorophenyl)-5-(2,4-dichlorophenyl)-1-methylimidazole

Product 1

HCID 10226761N-(Hexyl)-4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-1-methylimidazole-2-carboxamide

Procedure

Using essentially the same procedure as Example 33, but using n-hexyl isocyanate (0.040 mL, 0.30 mmol), 4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-1-methylimidazole (50 mg, 0.15 mmol) from Example 32, Step C was converted to the title compound after purification twice by Prep TLC (25% ethyl acetate in hexanes).

Sources & evidence

ORD record: ord-73ed897234124131b27998ecbd306353
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572785B2

Reaction notes

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