Dimethylformamide dimethyl acetal → HCID 22675057, compound

HRID 1634129Notes

Reaction equation

HRID 1634129 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.CO[CH:15](OC)[N:16]([CH3:18])[CH3:17]>CN(C=O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5](/[CH:9]=[CH:15]/[N:16]([CH3:18])[CH3:17])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 3437951,2-Dichloro-4-methyl-5-nitrobenzene

Product 1

HCID 22675057HCID 22675057, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 10.3 g (50 mmol) of 4,5-dichloro-2-nitrotoluene (Helv. Chim. Acta 1936, 19, 434-439) in a mixture of 11.9 g (100 mmol) N,N-dimethylformamide dimethylacetal in DMF (25 ml) was heated at 100° C. for 16 h. The dark reaction mixture was concentrated in vacuo, the residue diluted with methylene chloride and washed twice with water. The organic solution was dried over MgSO4, concentrated in vacuo affording 12.6 g (48 mmol, yield 96.5%) of the title compound as dark red to crude crystals.

Workup

  1. customThe dark reaction mixture
  2. concentrationwas concentrated in vacuo
  3. additionthe residue diluted with methylene chloride
  4. washwashed twice with water
  5. dry with materialThe organic solution was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-14ddd499784d4626bf0d0f81bbbeed85
Source dataset
uspto-grants-2003_01
Patent number
US06506758B2

Reaction notes

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