Acetyl chloride → HCID 73031688, compound

HRID 1663298Notes

Reaction equation

HRID 1663298 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[N:8][N:9]2[CH2:18][C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:19]([F:28])([C:24]([F:27])([F:26])[F:25])[C:20]([F:23])([F:22])[F:21])[CH:16]=3)[NH:11][C:10]2=[O:29])[CH:2]=1.[H-].[Na+].[C:32](Cl)(=[O:34])[CH3:33]>CN(C)C=O>[C:32]([N:11]1[C:12]2[C:17](=[CH:16][C:15]([C:19]([F:28])([C:24]([F:25])([F:26])[F:27])[C:20]([F:22])([F:21])[F:23])=[CH:14][CH:13]=2)[CH2:18][N:9]([N:8]=[CH:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:10]1=[O:29])(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 730165886-(1,1,1,2,3,3,3-Heptafluoropropan-2-yl)-3-{(E)-[(pyridin-3-yl)methylidene]amino}-3,4-dihydroquinazolin-2(1H)-one

Product 1

HCID 73031688HCID 73031688, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 10 ml of dimethylformamide was dissolved 0.84 g (2.0 mmol) of 3-(3-pyridylmethylideneamino)-3,4-dihydro-6-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-2(1H)-quinazolinone, and to the resulting solution was added 0.09 g (2.3 mmol) of sodium hydride (purity: 62.4%). The reaction was carried out at room temperature for 30 minutes, after which 0.19 g (2.4 mmol) of acetyl chloride was added and the reaction was carried out for 4 hours. After completion of the reaction, the reaction solution was poured into ice water and the desired compound was extracted with ethyl acetate (20 ml×3). The extract solution was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated in vacuo. The crude product thus obtained was purified by silica gel column chromatography (ethyl acetate−methanol 10:1) to obtain 0.51 g of the desired compound.

Workup

  1. waitthe reaction was carried out for 4 hours
  2. customAfter completion of the reaction
  3. extractionthe desired compound was extracted with ethyl acetate (20 ml×3)
  4. washThe extract solution was washed with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product thus obtained
  8. customwas purified by silica gel column chromatography (ethyl acetate−methanol 10:1)

Sources & evidence

ORD record
ord-933d6dec00bc44fcacf32123d49b965c
Source dataset
uspto-grants-2011_10
Patent number
US08034931B2

Reaction notes

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