Trichloroacetyl chloride → HCID 21285449, compound

HRID 2231632Notes

Reaction equation

HRID 2231632 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH3:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[Cl:20][C:21]([Cl:26])([Cl:25])[C:22](Cl)=[O:23]>C1(C)C=CC=CC=1>[CH3:14][C:12]1[CH:11]=[C:10]([CH3:15])[N:9]=[C:8]([N:1]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:22](=[O:23])[C:21]([Cl:26])([Cl:25])[Cl:20])[N:13]=1

Participants

6

Reactant 4

HCID 6420Trichloroacetyl chlorideHCID 24758Sodium hydrideHCID 91650PyrimethanilHCID 178418361HCID 178418361, compound

Product 1

HCID 21285449HCID 21285449, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

A solution of 2-anilino-4,6-dimethylpyrimidine (5 g) in toluene was added to a suspension of sodium hydride in oil (0.75 g of an 80% suspension) in toluene (100 ml) and the mixture was heated under reflux until evolution of hydrogen ceased. A solution of trichloroacetyl chloride (2.8 ml) in toluene (20 ml) was added dropwise at room temperature and the mixture heated at 80° for one hour. It was then worked up by filtration through silica using dichloromethane as eluent. The solvent was evaporated and the residue, after solidification, was recrystallised from ethyl acetate/diisopropyl ether to give N-(4,6-dimethylpyrimidin-2-yl)-N-phenyltrichloroacetamide, m.p. 125.5°-7°. (Compound 8).

Workup

  1. temperaturethe mixture was heated
  2. temperaturethe mixture heated at 80° for one hour
  3. filtrationIt was then worked up by filtration through silica
  4. customThe solvent was evaporated
  5. customthe residue, after solidification, was recrystallised from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-889a0ce9dadb42db96dd65986da64369
Source dataset
uspto-grants-1988_11
Patent number
US04783459

Reaction notes

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