Water → (2,2,5,5-Tetramethylcyclopentane-1-yl)carboxamide

HRID 231720Notes

Reaction equation

HRID 231720 reaction equation
[C:1]([CH:3]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH2:5][C:4]1([CH3:11])[CH3:10])#[N:2].[OH2:12]>[OH-].[Na+].CO>[CH3:8][C:7]1([CH3:9])[CH2:6][CH2:5][C:4]([CH3:11])([CH3:10])[CH:3]1[C:1]([NH2:2])=[O:12]

Participants

5

Reactant 2

HCID 962WaterHCID 140288492,2,5,5-Tetramethylcyclopentane-1-carbonitrile

Product 1

HCID 14028850(2,2,5,5-Tetramethylcyclopentane-1-yl)carboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

760 mg of 1-cyano-2,2,5,5-tetramethylcyclopentane was dissolved in 5 ml of aqueous 3N sodium hydroxide solution and 10 ml of MeOH, and the solution was stirred at room temperature for 10 hours. Then, 10 ml of water was added thereto, and the mixture was twice extracted with 30 ml of chloroform. The organic layers were combined, washed with 50 ml of water and concentrated under reduced pressure. The thus obtained residue was recrystallized from n-hexane, whereby 640 mg of (2,2,5,5-tetramethylcyclopentane-1-yl) carboxamide was obtained (m.p. 97.7° C.).

Workup

  1. extractionthe mixture was twice extracted with 30 ml of chloroform
  2. washwashed with 50 ml of water
  3. concentrationconcentrated under reduced pressure
  4. customThe thus obtained residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-52b98e1abc25427caf6061fbc076a678
Source dataset
uspto-grants-1989_07
Patent number
US04847390

Reaction notes

Loading…