Cesium acetate → 2-Acetoxymethyl-7-chloro-6-methyl-3,4-dihydroquinazolin-4-one

HRID 47850

반응식

HRID 47850 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:14])[NH:7][C:8]([CH2:12]Cl)=[N:9]2)=[CH:4][C:3]=1[CH3:15].[C:16]([O-:19])(=[O:18])[CH3:17].[Cs+]>CN(C=O)C>[C:16]([O:19][CH2:12][C:8]1[NH:7][C:6](=[O:14])[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([CH3:15])[CH:4]=2)[N:9]=1)(=[O:18])[CH3:17]

참가 물질

4

반응물 2

HCID 5152919Cesium acetateHCID 1354761257-chloro-2-(chloromethyl)-6-methylquinazolin-4(3H)-one

생성물 1

HCID 1354321952-Acetoxymethyl-7-chloro-6-methyl-3,4-dihydroquinazolin-4-one

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 7-chloro-2-chloromethyl-6-methyl-3,4-dihydroquinazolin-4-one (0.500 g, 2.06 mmol), anhydrous DMF (14 ml) and cesium acetate (1.58 g, 8.24 mmol) was placed in an oil bath preheated to 85° C., then stirred at this temperature for 2 hours and 15 min under argon. The reaction mixture was then allowed to cool to room temperature and the solvent was removed in vacuo. The residue was treated with hexanes (20 ml), collected by filtration, washed with hexanes (20 ml), water, and dried in vacuo over P2O5 (0.476 g, 87%), mp 220-225° C., 1H-NMR (DMSO-d6) 2.14 (s, 3H, CH3CO), 2.45 (s, 3H, 6-CH3), 4.95 (s, 2H, 2-CH2O), 7.70, 8.06 (2×s, 2H, 5-H and 8-H), 12.44 (s, 1H, N3—H).

후처리

  1. customwas placed in an oil bath
  2. custompreheated to 85° C.
  3. customthe solvent was removed in vacuo
  4. additionThe residue was treated with hexanes (20 ml)
  5. filtrationcollected by filtration
  6. washwashed with hexanes (20 ml), water
  7. dry with materialdried in vacuo over P2O5 (0.476 g, 87%), mp 220-225° C., 1H-NMR (DMSO-d6) 2.14 (s, 3H, CH3CO), 2.45 (s, 3H, 6-CH3), 4.95 (s, 2H, 2-CH2O), 7.70, 8.06 (2×s, 2H, 5-H and 8-H), 12.44 (s, 1H, N3—H)

출처 및 근거

ORD 기록
ord-bc4db9a4f67d43ceb7889c8db31e678b
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699861B1

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