Sodium Hydroxide → 5-(4-Methyl-4-nitropentyl)hydantoin

HRID 1744033Notes

Reaction equation

HRID 1744033 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].[OH-].[Na+].[H][H]>[C].[Pd].CO>[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 14798Sodium HydroxideHCID 695837495-(4-Methyl-4-nitropentylidene)hydantoinHCID 178418361HCID 178418361, compound

Product 1

HCID 99427025-(4-Methyl-4-nitropentyl)hydantoinYield 72.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst2×HCID 887MethanolSolvent

Procedure

Methanol (200 ml) was added to 5-(4-methyl-4-nitropentylidene)hydantoin (25.85 g, 114 mmol) and 27% aqueous sodium hydroxide solution was added to adjust the pH to 10 for dissolution. Palladium-carbon (1.1 g) and hydrogen were added for reduction. After the reaction, palladium-carbon was filtered off and methanol was evaporated by concentration under reduced pressure. Water (50 ml) was added and the pH was adjusted to 2 with concentrated hydrochloric acid. The precipitated crystals were separated and dried to give 5-(4-methyl-4-nitropentyl)hydantoin (19.02 g, 83 mmol, yield 72.9%).

Workup

  1. additionwas added
  2. dissolutionfor dissolution
  3. filtrationwas filtered off
  4. custommethanol was evaporated by concentration under reduced pressure
  5. additionWater (50 ml) was added
  6. customThe precipitated crystals were separated
  7. customdried

Sources & evidence

ORD record
ord-46531d72c6814c1ab3f77878c464fec6
Source dataset
uspto-grants-2006_03
Patent number
US07012152B2

Reaction notes

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