Thiophenol → HCID 15676628, compound

HRID 483612Notes

Reaction equation

HRID 483612 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].C([N:17]1[C:21](=[O:22])[C:20]([CH:24]([CH3:26])[CH3:25])([CH3:23])[N:19]=[C:18]1[C:27]1[N:36]=[CH:35][C:34]([CH2:37]Br)=[CH:33][C:28]=1[C:29]([O:31][CH3:32])=[O:30])(=O)C1C=CC=CC=1.[Cl-].[NH4+]>CO>[CH:24]([C:20]1([CH3:23])[C:21](=[O:22])[NH:17][C:18]([C:27]2[N:36]=[CH:35][C:34]([CH2:37][S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:33][C:28]=2[C:29]([O:31][CH3:32])=[O:30])=[N:19]1)([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 15676627HCID 15676627, compound

Product 1

HCID 15676628HCID 15676628, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of thiophenol, sodium salt and methanol is added to a solution of 2-(1-benzoyl-4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-(bromomethyl)nicotinic acid, methyl ester (14.08 g, 0.0298 mol) and methanol. The reaction mixture is stirred for 15 hours at room temperature, acidified with ammonium chloride (5 g, 0.0869 mol) and concentrated in vacuo to yield an oil. The oil is chromatographed using silica gel and hexanes/ethyl acetate (3:1) to (1:1) as eluant to give the title compound as a yellow solid (8.32 g, 55%), mp 135°-138° C., identified by IR and NMR spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. customto yield an oil
  3. customThe oil is chromatographed

Sources & evidence

ORD record
ord-7de7604c13ac4fb0ad1c226623b638f6
Source dataset
uspto-grants-1993_07
Patent number
US05225564

Reaction notes

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