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

HRID 47850ノート

反応式

HRID 47850 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-bc4db9a4f67d43ceb7889c8db31e678b
出典データセット
uspto-grants-2004_03
特許番号
US06699861B1

反応ノート

読み込み中…