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

HRID 2175698노트

반응식

HRID 2175698 반응식
[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]

참가 물질

6

반응물 3

HCID 6577Chloroacetyl chlorideHCID 8635Methyl AnthranilateHCID 516892Sodium Bicarbonate

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c920318cc0dd485d87b264c5e551b0d8
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062076B2

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