Hydrochloric Acid → N'-[6-(4-methylphenyl)-5-phenyl-2-(trifluoromethyl)pyrimidin-4-yl]acetohydrazide

HRID 2250334Notes

Reaction equation

HRID 2250334 reaction equation
[NH:1]([C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:7]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[N:6]=[C:5]([C:22]([F:25])([F:24])[F:23])[N:4]=1)[NH2:2].N1C=CC=CC=1.[C:32](Cl)(=[O:34])[CH3:33].Cl>ClCCl>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([C:7]2[N:6]=[C:5]([C:22]([F:25])([F:24])[F:23])[N:4]=[C:3]([NH:1][NH:2][C:32](=[O:34])[CH3:33])[C:8]=2[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 103828694-Hydrazino-6-(4-methylphenyl)-5-phenyl-2-(trifluoromethyl)pyrimidine

Product 1

HCID 59641749N'-[6-(4-methylphenyl)-5-phenyl-2-(trifluoromethyl)pyrimidin-4-yl]acetohydrazideYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydrazino-6-(4-methylphenyl)-5-phenyl-2-(trifluoromethyl)pyrimidine (0.23 g, 0.66 mmol) (synthesized according to the procedure described in example 22) in dichloromethane (5 ml) and pyridine (0.06 g, 0.8 mmol), acetyl chloride (0.6 g, 0.7 mmol) was added dropwise at room temperature over a period of ten minutes under stirring. Stirring was continued for two hours and the resultant reaction mass was poured onto ice-water mixture and neutralised with hydrochloric acid. The reaction mixture was extracted with dichloromethane. The organic extract was washed with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the title compound (0.2 g, 77.9%, HPLC purity 99.4%), mp: 147-152° C.

Workup

  1. stirringStirring
  2. customthe resultant reaction mass
  3. extractionThe reaction mixture was extracted with dichloromethane
  4. extractionThe organic extract
  5. washwas washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-79bd6969778d4f0c802a74bb2dde6230
Source dataset
uspto-grants-2008_01
Patent number
US07317014B2

Reaction notes

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