Dimethyl Sulfate → 2-(Methylthio)benzo[d]oxazol-6-ol

HRID 624091Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 624091
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[O:8][C:4]=2[CH:3]=1.[C:12](=O)(O)[O-].[Na+].S(OC)(OC)(=O)=O>O>[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([S:9][CH3:12])[O:8][C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 516892Sodium BicarbonateHCID 178515778HCID 178515778, Verbindung

Produkt 1

HCID 210778082-(Methylthio)benzo[d]oxazol-6-olAusbeute 25,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 6-hydroxy-2-mercaptobenzoxazole (165 mg), sodium bicarbonate (84 mg) and dimethyl sulfate (94 μl) was dissolved in water (2 ml) with stirring and under an argon atmosphere. The reaction mixture was stirred at RT overnight and HPLC showed that all starting material was gone. The reaction mixture was evaporated to dryness to give a dark brown solid (one can also extract the reaction mixture with chloroform to give the crude product). Chromatography on silica gel using 10% ethyl acetate/hexane gave the pure product as a near-white crystalline solid (45 mg, 25%).

Aufarbeitung

  1. stirringThe reaction mixture was stirred at RT overnight
  2. customThe reaction mixture was evaporated to dryness
  3. customto give a dark brown solid (one
  4. extractioncan also extract the reaction mixture with chloroform
  5. customto give the crude product)

Quellen und Nachweise

ORD-Eintrag
ord-f831a6fcb1b0468fa7c5dfa86c2d4c9d
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303026B2

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