Potassium Hydroxide → (E)-3-[2-n-Butyl-1-{(4-carboethoxyphenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic Acid

HRID 37009Notes

Reaction equation

HRID 37009 reaction equation
C(C1N(CC2C=CC(C(OC)=O)=CC=2Cl)C(C=O)=CN=1)CCC.C(O[C:27](=O)[CH:28]([C:35]([OH:37])=[O:36])[CH2:29][C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)C.[CH2:39]([C:43]1[N:44]([CH2:50][C:51]2[CH:56]=[CH:55][C:54]([C:57]([O:59][CH2:60][CH3:61])=[O:58])=[CH:53][CH:52]=2)[C:45](C=O)=[CH:46][N:47]=1)[CH2:40][CH2:41][CH3:42].[OH-].[K+].[Cl-].[Li+].C(C1N(CC2C=CC=CC=2Cl)C(/C=C(\CC2SC=CC=2)/C(O)=O)=CN=1)CCC>O.C(O)C.CN(C)C=O>[CH2:39]([C:43]1[N:44]([CH2:50][C:51]2[CH:52]=[CH:53][C:54]([C:57]([O:59][CH2:60][CH3:61])=[O:58])=[CH:55][CH:56]=2)[C:45](/[CH:27]=[C:28](\[CH2:29][C:30]2[S:31][CH:32]=[CH:33][CH:34]=2)/[C:35]([OH:37])=[O:36])=[CH:46][N:47]=1)[CH2:40][CH2:41][CH3:42]

Participants

8

Reactant 5

HCID 14797Potassium HydroxideHCID 433294Lithium ChlorideHCID 100474443-[2-Butyl-3-(2-chloro-benzyl)-3H-imidazol-4-yl]-2-thiophen-2-ylmethyl-acrylic acidHCID 19919877Methyl 4-[(2-butyl-5-formyl-1H-imidazol-1-yl)methyl]-3-chlorobenzoateHCID 867465512-n-Butyl-1-[(4-carboethoxyphenyl)methyl]imidazole-5-aldehyde ethyl 2-carboxy-3-(2-thienyl)propionate

Product 1

HCID 14952934(E)-3-[2-n-Butyl-1-{(4-carboethoxyphenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoic Acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 19096565Water ethanolSolvent

Procedure

The title compound was prepared following the procedure of Example 42 replacing 2-n-butyl-1-[(4-carbomethoxy-2-chlorophenyl)methyl]imidazole-5-aldehyde with 2-n-butyl-1-[(4-carboethoxyphenyl)methyl]imidazole-5-aldehyde ethyl 2-carboxy-3-(2-thienyl)propionate and potassium hydroxide in water-ethanol at ambient temperature with lithium chloride in dimethylformamide at 80°-125° C.; mp 129°-131° C. (d).

Workup

  1. customat ambient temperature
  2. customat 80°-125° C.

Sources & evidence

ORD record
ord-1b2e688c79034bb7807ae0da454cd15d
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

Loading…