Thiophenol → HCID 15676628, compound

HRID 2248242Notes

Reaction equation

HRID 2248242 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-232f66af97284460adc4a65dab49ae0e
Source dataset
uspto-grants-1991_08
Patent number
US05039333

Reaction notes

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