Nitroethane → 1-Methylsulfanyl-4-(2-nitro-propenyl)-benzene

HRID 908158Notes

Reaction equation

HRID 908158 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.C([O-])(=O)C.[NH4+].[N+:16]([CH2:19][CH3:20])([O-:18])=[O:17]>>[CH3:1][S:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:19]([N+:16]([O-:18])=[O:17])[CH3:20])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6587NitroethaneHCID 769854-(Methylthio)benzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 28259171-Methylsulfanyl-4-(2-nitro-propenyl)-benzene

Procedure

A stirred solution of 4-methylsulfanyl-benzaldehyde (5.0 g, 28.8 mmol) and ammonium acetate (0.666 g, 8.6 mmol) in nitroethane (17 ml, 236 mmol) is heated at reflux for 5 hours. The solvent is removed and the residue is dissolved in CHCl3 (100 ml) and washed with water (100 ml) followed by brine (100 ml). After drying (MgSO4) the solvent is removed to give the title compound as a yellow solid which is used crude in the next step.

Workup

  1. temperatureat reflux for 5 hours
  2. customThe solvent is removed
  3. dissolutionthe residue is dissolved in CHCl3 (100 ml)
  4. washwashed with water (100 ml)
  5. dry with materialAfter drying (MgSO4) the solvent
  6. customis removed

Sources & evidence

ORD record
ord-d9d5e82ce36f4b93ad4056aa3cb08b40
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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