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

HRID 470985ノート

反応式

HRID 470985 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 (1.8 mL) was added dropwise to a stirred mixture of 1-(3-amino-4-(benzyloxy)-2-hydroxyphenyl)ethanone (example 11, step c) (5.2 g) and sodium hydrogen carbonate (3.74 g) in DMF (30 mL) and then stirred for 2 h. Cesium carbonate (7.90 g) was added and the mixture 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 sulphate, filtered and evaporated under vacuum. The solid residue was treated with diethyl ether, filtered and dried to afford the subtitled compound as a beige solid. Yield 5.7 g.

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 sulphate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. additionThe solid residue was treated with diethyl ether
  9. filtrationfiltered
  10. customdried

出典と根拠

ORDレコード
ord-2245209a3ae342e59b432295b548beae
出典データセット
uspto-grants-2014_01
特許番号
US08629271B2

反応ノート

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