Methanol → 1-(Ethoxycarbonylaminocarbonyl)-2-(3,5-dimethoxy-4-hydroxyphenyl)-4,5-bis(4-diethylaminophenyl)imidazole

HRID 373731

Reaction equation

HRID 373731 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[NH:13][C:14]([C:28]3[CH:33]=[CH:32][C:31]([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])=[CH:30][CH:29]=3)=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[CH:19][CH:18]=3)[N:16]=2)[CH:6]=[C:7]([O:10][CH3:11])[C:8]=1[OH:9].[CH2:39]([O:41][C:42]([N:44]=[C:45]=[O:46])=[O:43])[CH3:40].CO>C(Cl)(Cl)Cl>[CH2:39]([O:41][C:42]([NH:44][C:45]([N:13]1[C:14]([C:28]2[CH:33]=[CH:32][C:31]([N:34]([CH2:37][CH3:38])[CH2:35][CH3:36])=[CH:30][CH:29]=2)=[C:15]([C:17]2[CH:18]=[CH:19][C:20]([N:23]([CH2:24][CH3:25])[CH2:26][CH3:27])=[CH:21][CH:22]=2)[N:16]=[C:12]1[C:5]1[CH:6]=[C:7]([O:10][CH3:11])[C:8]([OH:9])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:46])=[O:43])[CH3:40]

Participants

5

Reactant 3

HCID 887MethanolHCID 300166ethyl N-carbonylcarbamate2×HCID 1360065552-(3,5-Dimethoxy-4-hydroxyphenyl)-4,5-bis(4-diethylaminophenyl)imidazole

Product 1

HCID 1360327571-(Ethoxycarbonylaminocarbonyl)-2-(3,5-dimethoxy-4-hydroxyphenyl)-4,5-bis(4-diethylaminophenyl)imidazoleYield 61.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 20 ml of chloroform, 0.8 g of 2-(3,5-dimethoxy-4-hydroxyphenyl)-4,5-bis(4-diethylaminophenyl)imidazole obtained in Example 1 (2) was dissolved. Then, 0.7 g of ethoxycarbonyl isocyanate (mfd. by Aldrich Chemical Co. Inc.) was added to the resulting solution and the reaction was carried out at room temperature for 5 hours with stirring. After the reaction, 5 ml of methanol was added to the reaction solution to decompose excess ethoxycarbonyl isocyanate, followed by removal of the solvent by distillation under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: a mixed solvent of ethyl acetate and n-hexane) to give 0.6 g of green crystals of 1-(ethoxycarbonylaminocarbonyl)-2-(3,5-dimethoxy-4-hydroxyphenyl)-4,5-bis(4-diethylaminophenyl)imidazol having a m.p. of 60° C.

Workup

  1. additionwas added to the reaction solution
  2. customfollowed by removal of the solvent by distillation under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-64a58222fb414e52912b0cce693b31ca
Source dataset
uspto-grants-1992_11
Patent number
US05164512

Linked notes

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