Dimethylformamide dimethyl acetal → HCID 22675057, compound

HRID 1005923Notes

Reaction equation

HRID 1005923 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, then concentrated in vacuo affording 12.6 g (48 mmol, yield 96.5%) of the crude title compound as dark red 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-06f2e6cbaf0a4987a61bafcfcd5bd63a
Source dataset
uspto-grants-2004_09
Patent number
US06787550B1

Reaction notes

Loading…