Chloroacetyl chloride → 2H-1,4-Benzoxazine-8-carboxylic acid, 3,4-dihydro-3-oxo-, ethyl ester

HRID 429670

反応式

HRID 429670 の反応式
[NH2:1][C:2]1[C:3]([OH:13])=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(=O)([O-])O.[Na+].Cl[CH2:20][C:21](Cl)=[O:22]>[Br-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.C(Cl)(Cl)Cl>[O:13]1[C:3]2[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:10][CH:11]=[CH:12][C:2]=2[NH:1][C:21](=[O:22])[CH2:20]1

参加物

6

反応物 3

HCID 6577Chloroacetyl chloride2 回HCID 516892Sodium BicarbonateHCID 22096614Ethyl 3-amino-2-hydroxybenzoate

生成物 1

HCID 183551602H-1,4-Benzoxazine-8-carboxylic acid, 3,4-dihydro-3-oxo-, ethyl ester収率 75.4%

試薬・触媒・溶媒 2

HCID 2724282Benzenemethanaminium, N,N,N-tributyl-, bromide触媒HCID 6212Chloroform溶媒3 回

反応条件

温度
60 °C

実験手順

To a solution of ethyl 3-amino-2-hydroxybenzoate (500 mg), sodium hydrogen carbonate (927 mg) and benzyltributylammonium bromide (983 mg) in chloroform (10 ml) was added dropwise chloroacetyl chloride (374 mg) in chloroform (3 ml) under ice bath cooling. The reaction mixture was stirred at ambient temperature for 1 hour and at 60° C. for 2 hours. To the reaction mixture was added dropwise chloroacetyl chloride (312 mg) in chloroform (3 ml) under ice bath cooling and stirred at 60° C. for 2 hours. After the reaction mixture was concentrated in vacuo, the residue was diluted with chloroform and saturated sodium hydrogen carbonate aqueous solution. The organic layer was separated and washed with brine. The solution was dried over magnesium sulfate and concentrated in vacuo to give ethyl 2H-1,4-benzoxazin-3-one-8-carboxylate (460 mg).

後処理

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirred at 60° C. for 2 hours
  4. concentrationAfter the reaction mixture was concentrated in vacuo
  5. additionthe residue was diluted with chloroform and saturated sodium hydrogen carbonate aqueous solution
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialThe solution was dried over magnesium sulfate
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e0ff44ebd9e34e3dae7a7c5c8bd7789a
出典データセット
uspto-grants-2001_11
特許番号
US06316482B1

関連ノート

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