Potassium Hydroxide → 2-[(2-Oxo-1-imidazolidinyl)methyl]-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinone

HRID 1252607Notes

Reaction equation

HRID 1252607 reaction equation
[OH-].[K+].Cl[CH2:4][CH2:5][NH:6][C:7]([NH:9][CH2:10][C:11]1(CC2C=CC=CC=2)[CH2:16][C:15](=[O:17])[C:14]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:13][NH:12]1)=[O:8]>C(O)C>[O:8]=[C:7]1[NH:6][CH2:5][CH2:4][N:9]1[CH2:10][C:11]1[N:12]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=[C:14]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:15](=[O:17])[CH:16]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 201403872-[[[[(2-Chloroethyl)amino]carbonyl]amino]methyl]-5-(phenylmethoxy)-2-(phenylmethyl)-4(1H)-pyridinone

Product 1

HCID 141824752-[(2-Oxo-1-imidazolidinyl)methyl]-5-(phenylmethoxy)-1-(phenylmethyl)-4(1H)-pyridinoneYield 91.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 7.29 g (0.13 mol) of potassium hydroxide in 500 ml of ethanol was added dropwise to a mixture of 60.8 g (0.13 mol) of 2-[[[[(2-chloroethyl)amino]carbonyl]amino]methyl]-5-(phenylmethoxy)-2-(phenylmethyl)-4(1H)-pyridinone and 1.3 l of ethanol. The reaction mixture was heated to reflux for three hours and the solvent evaporated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of ethyl acetate and methanol (7:3) as eluent, yielding 23.1 g of product, which was further purified by recrystallization from acetonitrile, yielding 17.0 g of the title compound, melting point 190° C., dec.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for three hours
  3. customthe solvent evaporated in vacuo
  4. customThe residue was purified by column chromatography on silica gel using
  5. additiona mixture of ethyl acetate and methanol (7:3) as eluent

Sources & evidence

ORD record
ord-24df3aae7ae344eaa7f3c2a542fb18d7
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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