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

HRID 2175698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2175698
[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]

Komponenten

6

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 8635Methyl AnthranilateHCID 516892Sodium Bicarbonate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c920318cc0dd485d87b264c5e551b0d8
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09062076B2

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