Chloroacetyl chloride → 8-Acetyl-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 909867ノート

反応式

HRID 909867 の反応式
Cl[CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[C:8]([OH:24])=[C:9]([C:21](=[O:23])[CH3:22])[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:21]([C:9]1[C:8]2[O:24][CH2:2][C:3](=[O:4])[NH:6][C:7]=2[C:12]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)(=[O:23])[CH3:22]

参加物

6

反応物 4

HCID 6577Chloroacetyl chlorideHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 579892521-(3-Amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone

生成物 1

HCID 579889708-Acetyl-5-(benzyloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

2-Chloroacetyl chloride (1.77 mL) was added dropwise to a stirred mixture of 1-(3-amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone (5.2 g) and sodium hydrogen carbonate (3.74 g) in DMF (30 mL) and then stirred for a further 2 h. Cesium carbonate (7.90 g) was added and heated at 100° C. for 20 h. The mixture was cooled to ambient temperature, quenched with water (500 mL), extracted with ethyl acetate (2×200 mL), washed with water (3×300 mL) and brine, dried over anhydrous sodium sulfate, filtered and evaporated under vacuum. The solid residue was treated with ether, filtered and dried to afford the subtitled compound as a beige solid (5.7 g). 1H NMR (400 MHz, DMSO-d6) δ 10.33 (s, 1H), 7.55 (m, 2H), 7.39 (m, 2H), 7.34 (d, J=8.8 Hz, 1H), 7.33 (m, 1H), 6.89 (d, J=9.2 Hz, 1H), 5.27 (s, 2H), 4.67 (s, 2H), 3.32 (s, 3H).

後処理

  1. temperatureThe mixture was cooled to ambient temperature
  2. customquenched with water (500 mL)
  3. extractionextracted with ethyl acetate (2×200 mL)
  4. washwashed with water (3×300 mL) and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. additionThe solid residue was treated with ether
  9. filtrationfiltered
  10. customdried

出典と根拠

ORDレコード
ord-9881e974e81e46caad3fe994784f786d
出典データセット
uspto-grants-2011_09
特許番号
US08017602B2

反応ノート

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