Hydrochloric Acid → Methyl 4-[methyl(3-phenylpropanoyl)amino]benzoate

HRID 642143

Reaktionsgleichung

Reaktionsgleichung von HRID 642143
[CH3:1][NH:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[C:13](Cl)(=[O:22])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.Cl>N1C=CC=CC=1>[CH3:1][N:2]([C:13](=[O:22])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 64801Benzenepropanoyl chlorideHCID 140375Methyl 4-methylaminobenzoate

Produkt 1

HCID 9814733Methyl 4-[methyl(3-phenylpropanoyl)amino]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-methylaminobenzoate (1.0 g, 6.05 mmol) in anhydrous pyridine (20 mL) was added dropwise hydrocinnamoyl chloride (1080 μL) at rt. After 16 hrs water (5 mL) was added and the resulting mixture was stirred for 1 hr at rt. The resulting mixture was poured into water (300 mL) and HCl (5 N, 50 mL) was added. The compound was extracted with AcOEt (2×300 mL) and washed with a saturated aqueous solution of NaHCO3 (150 mL). The combined organic layers were dried over MgSO4 and evaporated under vacuo to give the title compound (1.80 g) was obtained as a beige solid (95%) in 95.3% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Aufarbeitung

  1. additionwas added
  2. extractionThe compound was extracted with AcOEt (2×300 mL)
  3. washwashed with a saturated aqueous solution of NaHCO3 (150 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customevaporated under vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0f3b38928b8044e5bcb67e914b504343
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696231B2

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