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

HRID 1744013Notes

Reaction equation

HRID 1744013 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].[H][H].CO>[C].[Pd].O.C(O)C>[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

7

Reactant 3

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

Product 1

HCID 99427025-(4-Methyl-4-nitropentyl)hydantoin

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

(viv) 5-(4-Methyl-4-nitropentylidene)hydantoin is reduced with a transition metal catalyst (such as palladium) and the like to give 5-(4-methyl-4-nitropentyl)hydantoin. For example, 5-(4-methyl-4-nitropentylidene)hydantoin is reacted with hydrogen gas upon addition of palladium-carbon (generally 0.1–5 mol %, preferably 0.5–2 mol %) in a mixed solvent of a water soluble solvent, such as methanol, ethanol and the like, and water for 1–12 h, preferably 2–5 h. The reaction solvent is concentrated to dryness to give 5-(4-methyl-4-nitropentyl)hydantoin. The obtained 5-(4-methyl-4-nitropentyl)hydantoin can be isolated and/or purified by a conventional method, such as chromatography and the like, but generally, can be used in the next step without isolation and/or purification.

Workup

  1. custompreferably 2–5 h
  2. concentrationThe reaction solvent is concentrated to dryness

Sources & evidence

ORD record
ord-3fe32f9992f749d4b8519bb2603485fd
Source dataset
uspto-grants-2006_03
Patent number
US07012152B2

Reaction notes

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