Acetone → {[(2-Methyl-1-nitropropan-2-yl)sulfanyl]methyl}benzene

HRID 1033822Notes

Reaction equation

HRID 1033822 reaction equation
[CH3:1][C:2]([CH3:4])=O.[CH2:5]([SH:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+:13]([CH3:16])([O-:15])=[O:14].N1CCCCC1>C1C=CC=CC=1.O>[CH2:5]([S:12][C:2]([CH3:4])([CH3:1])[CH2:16][N+:13]([O-:15])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 6375NitromethaneHCID 7509Benzyl mercaptanHCID 8082Piperidine

Product 1

HCID 14613816{[(2-Methyl-1-nitropropan-2-yl)sulfanyl]methyl}benzene

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

Acetone (25 g), benzyl mercaptan (53 g), nitromethane (26.2 g), and piperidine (8 cm3) were dissolved in benzene (150 cm3) and the mixture heated under reflux with azeotropic removal of water. After 48 h the reaction mixture was allowed to cool and washed first with dilute hydrochloric acid, then with water. The remaining solution was dried (MgSO4) and the solvent then removed under reduced pressure to give the nitro system (76.5 g, 85%). This material was sufficiently pure to be used without further purification.

Workup

  1. temperaturethe mixture heated
  2. temperatureto cool
  3. washwashed first with dilute hydrochloric acid
  4. dry with materialThe remaining solution was dried (MgSO4)
  5. customthe solvent then removed under reduced pressure

Sources & evidence

ORD record
ord-f1507ad9f5b4440ba0987a3e0f60a33b
Source dataset
uspto-grants-1994_05
Patent number
US05312904

Reaction notes

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