Nitromethane → 1,5-Dichloro-3-methoxy-2-(2-nitrovinyl)benzene

HRID 1021347Notes

Reaction equation

HRID 1021347 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([O:11][CH3:12])[C:3]=1[CH:4]=O.Cl.CN.C([O-])(=O)C.[Na+].[N+:21]([CH3:24])([O-:23])=[O:22]>O.C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[C:6]([O:11][CH3:12])[C:3]=1[CH:4]=[CH:24][N+:21]([O-:23])=[O:22]

Participants

7

Reactant 4

HCID 6375NitromethaneHCID 517045Sodium AcetateHCID 6364545Methylamine hydrochlorideHCID 128028802,4-Dichloro-6-methoxybenzaldehyde

Product 1

HCID 670808981,5-Dichloro-3-methoxy-2-(2-nitrovinyl)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 2,4-dichloro-6-methoxybenzaldehyde (0.51 g; 2.5 mmol), methylamine hydrochloride (0.11 g; 1.6 mmol) and sodium acetate (0.13 g; 1.6 mmol) in 3 mL of nitromethane was stirred at ambient temperature. After stirring for 15.5 hours the mixture was diluted with 20 mL water and 40 mL DCM, and then transferred to a separatory funnel. After shaking, the organic layer was dried over sodium sulfate and evaporated to give 0.57 g of 1,5-dichloro-3-methoxy-2-(2-nitrovinyl)benzene as a light yellow solid. MS (apci, neg) m/z=247

Workup

  1. stirringAfter stirring for 15.5 hours the mixture
  2. customtransferred to a separatory funnel
  3. stirringAfter shaking
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-5a066c090e59411b8624256d97f4c58f
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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