Dimethylformamide → HCID 18923653, compound

HRID 1290165Notes

Reaction equation

HRID 1290165 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:13]([CH3:22])[C:14]1[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].CN(C)[CH:27]=[O:28]>>[CH2:6]([N:13]([CH3:22])[C:14]1[CH:15]=[C:16]([Cl:21])[C:17]([CH:27]=[O:28])=[C:18]([Cl:20])[CH:19]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 18923724HCID 18923724, compound

Product 1

HCID 18923653HCID 18923653, compound

Procedure

Phosphoryl chloride (12.7 ml) was dropwise added to N,N-dimethylformamide (70 ml), and the mixture was stirred for 30 minutes at ambient temperature. A solution of N-benzyl-3,5-dichloro-N-methylaniline (7.26 g) in N,N-dimethylformamide (30 ml) was dropwise added thereto, and the mixture was stirred for 30 minutes at ambient temperature and then for 30 minutes at 50° C. The reaction mixture was neutralized with 1N aqueous sodium hydroxide solution and extracted with ethyl acetate. The organic solution was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by a flash chromatography (ethyl acetate: n-hexane=1:6, V/V) to give N-benzyl-3,5-dichloro-4-formyl-N-methylaniline (5.70 g).

Workup

  1. stirringthe mixture was stirred for 30 minutes at ambient temperature
  2. waitfor 30 minutes at 50° C
  3. extractionextracted with ethyl acetate
  4. washThe organic solution was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by a flash chromatography (ethyl acetate: n-hexane=1:6, V/V)

Sources & evidence

ORD record
ord-c14df4096f2a4d14af7e1ab7806d6c94
Source dataset
uspto-grants-1998_05
Patent number
US05750699

Reaction notes

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