Nitroethane → 1-Chloro-2-nitro-4-[(1E)-2-nitro-1-propen-1-yl]benzene

HRID 2382610Notes

Reaction equation

HRID 2382610 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[Cl:12])[CH:7]=O)([O-:3])=[O:2].C([O-])(=O)C.[NH4+].[N+:18]([CH2:21][CH3:22])([O-:20])=[O:19]>C(Cl)Cl>[Cl:12][C:11]1[CH:10]=[CH:9][C:6](/[CH:7]=[C:21](/[N+:18]([O-:20])=[O:19])\[CH3:22])=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6587NitroethaneHCID 855054-Chloro-3-nitrobenzaldehydeHCID 517165Ammonium Acetate

Product 1

HCID 137762661-Chloro-2-nitro-4-[(1E)-2-nitro-1-propen-1-yl]benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of 3-Nitro-4-chlorobenzaldehyde (10 g, 53.89 mmol), ammonium acetate (1.39 g, 18 mmol) and nitroethane (31.3 ml, 432 mmol) is heated at reflux (80° C.) overnight. After cooling to room temperature the reaction mixture is concentrated if vacuo to give a solid which is dissolved in DCM (200 ml) and washed with water (3×200 ml), followed by brine (200 ml). The organic portion is dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as an orange solid.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. concentrationis concentrated if vacuo
  4. customto give a solid which
  5. washwashed with water (3×200 ml)
  6. dry with materialThe organic portion is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d01c4645e48d4893b364a106fc13dade
Source dataset
uspto-grants-2012_09
Patent number
US08263585B2

Reaction notes

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