Water → Methyl 2-amino-5-chloro-3-methylbenzenecarboxylate

HRID 490976

Reaktionsgleichung

Reaktionsgleichung von HRID 490976
[NH2:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].S(Cl)([Cl:16])(=O)=O.O.[OH-].[Na+]>C(#N)C>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[C:9]([Cl:16])[CH:10]=[C:11]([CH3:12])[C:2]=1[NH2:1]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24648Sulfuryl chlorideHCID 2763406Methyl 3-methylanthranilate

Produkt 1

HCID 12744623Methyl 2-amino-5-chloro-3-methylbenzenecarboxylateAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

The solution prepared in Step A (195 g, 475 mmol) was diluted with acetonitrile (50 mL), and heated to 50° C. Then a solution of sulfuryl chloride (70.6 g, 523 mmol) in acetonitrile (100 mL) was added over 3.25 h at 50-55° C. Immediately after completion of the addition, the mixture was cooled to 5° C., water (150 g) was added, and the pH of the solution was adjusted to 6.0 by slow addition of 50% aqueous sodium hydroxide (103 g). After stirring for 10 minutes at this temperature, the organic layer was separated, and the aqueous layer was extracted with acetonitrile (50 mL). The organic layers were combined, dried (MgSO4), and partially evaporated to a weight of 193.7 g. Quantitative HPLC of this solution showed 41.5 wt % of the title compound (80.4 g, 84.8% yield).

Aufarbeitung

  1. additionImmediately after completion of the addition
  2. temperaturethe mixture was cooled to 5° C.
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with acetonitrile (50 mL)
  5. dry with materialdried (MgSO4)
  6. custompartially evaporated to a weight of 193.7 g

Quellen und Nachweise

ORD-Eintrag
ord-26bfaa70e7bc4b96b215343277478660
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528260B2

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