Dimethylcarbamoyl Chloride → 2-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-N,N-dimethylacetamide

HRID 547453

反応式

HRID 547453 の反応式
[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH3:31][N:32]([CH3:36])[C:33](Cl)=[O:34]>O1CCCC1>[CH2:1]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][C:13]([Cl:19])=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH2:20][C:33]([N:32]([CH3:36])[CH3:31])=[O:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 583781963-benzyl-7-chloro-2-methylquinazolin-4(3H)-one

生成物 1

HCID 583781752-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-N,N-dimethylacetamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

3-Benzyl-7-chloro-2-methylquinazolin-4 (3H)-one (2 g, 1 eq.) was dissolved in tetrahydrofuran (20 ml). The solution was cooled to −78° C. for 15 minutes. Lithium hexamethyl disilazide (LHMDS) was added slowly and the mixture was stirred at −78° C. for 45 minutes. Dimethylcarbamyl chloride was added and the mixture was stirred at −78° C. for 1 h. The reaction was allowed to warm to room temperature and stirred for 3 h. The solvent was evaporated and the resulting solid was dissolved in ethyl acetate. The ethyl acetate layer was washed with water, saturated sodium bicarbonate, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated. The crude product was purified by flash chromatography to give 2-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-N,N-dimethylacetamide (1.2 g) as a solid.

後処理

  1. stirringthe mixture was stirred at −78° C. for 1 h
  2. temperatureto warm to room temperature
  3. stirringstirred for 3 h
  4. customThe solvent was evaporated
  5. dissolutionthe resulting solid was dissolved in ethyl acetate
  6. washThe ethyl acetate layer was washed with water, saturated sodium bicarbonate, saturated sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-05603e43da654f5c8e17e84f8dc2034e
出典データセット
uspto-grants-2011_05
特許番号
US07939539B2

関連ノート

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