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

HRID 547453

반응식

HRID 547453 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-05603e43da654f5c8e17e84f8dc2034e
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939539B2

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