Methanol → 5-(4-Methyl-4-nitropentyl)hydantoin

HRID 1744032Notes

Reaction equation

HRID 1744032 reaction equation
[CH3:1][C:2]([N+:14]([O-:16])=[O:15])([CH3:13])[CH2:3][CH2:4][CH:5]=[C:6]1[NH:10][C:9](=[O:11])[NH:8][C:7]1=[O:12].CO.[H][H]>[C].[Pd].O>[CH3:13][C:2]([N+:14]([O-:16])=[O:15])([CH3:1])[CH2:3][CH2:4][CH2:5][CH:6]1[NH:10][C:9](=[O:11])[NH:8][C:7]1=[O:12]

Participants

6

Reactant 3

HCID 887MethanolHCID 695837495-(4-Methyl-4-nitropentylidene)hydantoinHCID 178418361HCID 178418361, compound

Product 1

HCID 99427025-(4-Methyl-4-nitropentyl)hydantoinYield 34.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 962WaterSolvent

Procedure

To 5-(4-methyl-4-nitropentylidene)hydantoin (3.15 g, 13.9 mmol) were added methanol (60 ml) and water (10 ml), and the mixture was reduced by the addition of palladium-carbon (2.2 g) and hydrogen. After the reaction, palladium-carbon was filtered off and the residue was concentrated to dryness. Decantation with water and dichloromethane gave 5-(4-methyl-4-nitropentyl)hydantoin (1.1 g).

Workup

  1. filtrationwas filtered off
  2. concentrationthe residue was concentrated to dryness

Sources & evidence

ORD record
ord-e10fd10134fd4f22a8172a50d95b590d
Source dataset
uspto-grants-2006_03
Patent number
US07012152B2

Reaction notes

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