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

HRID 468544Notes

Reaction equation

HRID 468544 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-4b9245397c254b1c88757546dfc4443b
Source dataset
uspto-grants-2014_01
Patent number
US08624025B2

Reaction notes

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