Ammonium Chloride → HCID 21906846、化合物

温度

-25 °C

Methanolic sodium methoxide solution (28%) (5 ml, 25.9 mmol) was diluted with MeOH (5 ml) and was cooled to −25° C. under nitrogen. A solution of 4-chloro-2-thiophenecarboxaldehyde (J Heterocyclic Chem, 1976, 13, 393; 1.1 g, 7.5 mmol) and methyl azidoacetate (3.0 g, 26.1 mmol) in MeOH (20 ml) was added dropwise, maintaining the temperature at −25° C. On completion of addition the solution was allowed to warm to 5° C. over a period of approximately 16 hours. The solution was added to saturated aqueous ammonium chloride (250 ml) and the mixture was extracted using DCM. The combined organic layers were concentrated at 0° C. The residue was taken up in xylene (30 ml) and this solution was added dropwise to xylene (120 ml) under reflux. The solution was heated under reflux for 30 minutes before being cooled and concentrated. The title compound was purified by a mixture of crystallisation (EtOAc/isohexane) and chromatography on a Bond Elut column eluting with a graduated solvent of 5–50% EtOAc in isohexane (640 mg, 40%). NMR (CDCl3) 9.1 (1H, br), 7.1 (2H, s), 3.9 (3H, s); m/z 214.3.

1. temperaturemaintaining the temperature at −25° C
2. additionOn completion of addition the solution
3. temperatureto warm to 5° C. over a period of approximately 16 hours
4. extractionthe mixture was extracted
5. concentrationThe combined organic layers were concentrated at 0° C
6. additionthis solution was added dropwise to xylene (120 ml)
7. temperatureunder reflux
8. temperatureThe solution was heated
9. temperatureunder reflux for 30 minutes
10. temperaturebefore being cooled
11. concentrationconcentrated
12. customThe title compound was purified by a mixture of crystallisation (EtOAc/isohexane) and chromatography on a Bond Elut column
13. washeluting with a graduated solvent of 5–50% EtOAc in isohexane (640 mg, 40%)

ORDレコード

ord-d6b20170f36e4085a4997b5f23e0b672

出典データセット

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07122567B2