Chloroacetyl chloride → 3-[4-(2-Chloroacetylamino)-3-hydroxyphenyl]acrylic acid ethyl ester

HRID 1108403Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1108403
[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[C:9]([OH:14])[CH:8]=1)[CH3:2].C([O-])(O)=O.[Na+].[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:23](=[O:24])[CH2:22][Cl:21])=[C:9]([OH:14])[CH:8]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 540473973-(4-Amino-3-hydroxyphenyl)-acrylic acid ethyl ester

Produkt 1

HCID 541602373-[4-(2-Chloroacetylamino)-3-hydroxyphenyl]acrylic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 11-3 (3.38 g, 16.3 mmol) in CHCl3 (80 mL) was added saturated NaHCO3 (50 mL) and it was then chilled to 0° C. A solution of chloroacetyl chloride (1.94 mL, 24.4 mmol) in CHCl3 (30 mL) was added dropwise to the chilled biphase. Upon addition completion, the reaction was stirred at 0° C. for 1 h. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to give 11-4 which was used without further purification in the next step.

Aufarbeitung

  1. additionUpon addition completion
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give 11-4 which
  8. customwas used without further purification in the next step

Quellen und Nachweise

ORD-Eintrag
ord-dd324a62acf3461f91b57b8eb64d2328
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06066648

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