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

HRID 1513300Notes

Reaction equation

HRID 1513300 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 210778082-(Methylthio)benzo[d]oxazol-6-olYield 25.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-03fd9f73b8b94fdab34031d6c9b25421
Source dataset
uspto-grants-2012_07
Patent number
US08217171B2

Reaction notes

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