N-[4-(2-Oxoimidazolidin-1-yl)phenyl]acetamide → 1-(4-Acetamidocyclohexyl)-2-imidazolidinone

HRID 979887Notes

Reaction equation

HRID 979887 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>O.[Rh]>[C:1]([NH:4][CH:5]1[CH2:6][CH2:7][CH:8]([N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])[CH2:9][CH2:10]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 13755487N-[4-(2-Oxoimidazolidin-1-yl)phenyl]acetamide

Product 1

HCID 137554881-(4-Acetamidocyclohexyl)-2-imidazolidinone

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 4213 g of 1-(p-acetamidophenyl)-2-imidazolidinone in 39,000 ml of water and 2930 g of 5% rhodium on carbon 50% wet with water is hydrogenated at 40°. The hydrogenation mixture is filtered, and the filtrate is concentrated in vacuo to dryness. The resulting solid is air-dried and then powdered. The crude product is recrystallized from 12,000 ml of acetone to give 1-(4-acetamidocyclohexyl)-2-imidazolidinone, m.p. 211°-230° as a mixture of cis and trans isomers.

Workup

  1. customis hydrogenated at 40°
  2. filtrationThe hydrogenation mixture is filtered
  3. concentrationthe filtrate is concentrated in vacuo to dryness
  4. customThe resulting solid is air-dried
  5. customThe crude product is recrystallized from 12,000 ml of acetone

Sources & evidence

ORD record
ord-6bd4abd283f54ef49448ca5b36f95abc
Source dataset
uspto-grants-1987_01
Patent number
US04634713

Reaction notes

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