Chloroacetyl chloride → Methyl 2-[(chloroacetyl)amino]benzoate

HRID 2175698ノート

反応式

HRID 2175698 の反応式
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])(O)=O.[Na+].[Cl:17][CH2:18][C:19](Cl)=[O:20]>C1COCC1.O>[Cl:17][CH2:18][C:19]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])=[O:20]

参加物

6

反応物 3

HCID 6577Chloroacetyl chlorideHCID 8635Methyl AnthranilateHCID 516892Sodium Bicarbonate

生成物 1

HCID 295954Methyl 2-[(chloroacetyl)amino]benzoate収率 96%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of methyl 2-aminobenzoate (906 mg, 6.0 mmol) and NaHCO3 (554.4 mg, 6.6 mmol) in THF (12 mL) and water (12 mL) at 0° C. was added 2-chloroacetyl chloride (806 mg, 7.2 mmol) dropwise. After 2 hours, the mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to afford the crude product. The residue was purified by flash chromatography to give methyl 2-(2-chloroacetamido)benzoate (1.31 g, 96%). LC-MS (ES-API); rt 8.65 min; m/z calculated for C10H10ClNO3 [M+Na]+ 250.0, found 250.0.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product
  6. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-c920318cc0dd485d87b264c5e551b0d8
出典データセット
uspto-grants-2015_06
特許番号
US09062076B2

反応ノート

読み込み中…