Hydrochloric Acid → Ethyl 1,3-benzothiazole-2-carboxylate

HRID 2306666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2306666
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[C:9](OCC)(=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11].O.Cl>CCO>[S:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:9]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7268Diethyl OxalateHCID 87132-Aminothiophenol

Produkt 1

HCID 640708Ethyl 1,3-benzothiazole-2-carboxylateAusbeute 36,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 2-aminothiophenol (10.7 mL, 0.1 mol) in diethyl oxalate (27.3 mL, 0.2 mol) is heated at reflux for 4 hr. The solution is cooled to rt and poured into a solution consisting of water (150 mL), conc. HCl (50 mL) and 95% EtOH (70 mL). With stirring, the oil dissolved and a solid formed. The solution is cooled in an ice bath, the solid is collected by vacuum filtration and the solids are washed with a solution consisting of EtOH/water (25/75) to afford a dark solid. This material is purified by crystallization from hot (68° C.) ligroin to yield ethyl 2-benzothiazolecarboxylate (7.5 g, 36%). Elemental analysis for C10H9NO2S: Calc: C, 57.95; H, 4.38; N, 6.76. Found: C, 57.99; H, 4.28; N, 6.78.

Aufarbeitung

  1. temperatureat reflux for 4 hr
  2. additionpoured into a solution
  3. dissolutionthe oil dissolved
  4. customa solid formed
  5. temperatureThe solution is cooled in an ice bath
  6. filtrationthe solid is collected by vacuum filtration
  7. washthe solids are washed with a solution
  8. customto afford a dark solid
  9. customThis material is purified by crystallization from hot (68° C.) ligroin

Quellen und Nachweise

ORD-Eintrag
ord-b6260acca8cb43dbbde125fc1e8e190f
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06828330B2

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