Dimethyl Sulfate → 304912-64-9

HRID 1356677Notes

Reaction equation

HRID 1356677 reaction equation
[OH-].[Na+].[NH2:3][C:4]1[CH:11]=[CH:10][C:9]([S:12][C:13]#N)=[CH:8][C:5]=1[C:6]#[N:7].[BH4-].[Na+].S(OC)(OC)(=O)=O>O.CO>[NH2:3][C:4]1[CH:11]=[CH:10][C:9]([S:12][CH3:13])=[CH:8][C:5]=1[C:6]#[N:7]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 18509302HCID 18509302, compound

Product 1

HCID 18509303304912-64-9Yield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (97%, 1.20 g (29.1 mmol)) was dissolved in a mixed solvent of water (4.0 ml) and methanol (20.0 ml). To this, 2-amino-5-thiocyanobenzonitrile (5.03 g (28.7 mmol) was added with stirring. To the resulting mixture, after 30 minutes' stirring under cooling with ice, sodium borohydride (90%, 0.60 g (14.3 mmol)) was added and further stirred for 30 minutes under cooling with ice. Then, dimethyl sulfate (95%, 3.0 ml (30.0 mmol)) was added dropwise. The resulting mixture was further stirred under cooling with ice for 30 minutes and at room temperature for 30 minutes, and then concentrated under reduced pressure. Water was added to the residue and the mixture was extracted with diethyl ether. The extract was washed twice with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give 4.73 g (100%) of 2-amino-5-methylthiobenzonitrile as yellow crystals.

Workup

  1. stirringTo the resulting mixture, after 30 minutes' stirring
  2. additionwas added
  3. stirringfurther stirred for 30 minutes
  4. temperatureunder cooling with ice
  5. stirringThe resulting mixture was further stirred
  6. concentrationconcentrated under reduced pressure
  7. additionWater was added to the residue
  8. extractionthe mixture was extracted with diethyl ether
  9. washThe extract was washed twice with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a182668d54d04e9e9d734e01afe08220
Source dataset
uspto-grants-2003_07
Patent number
US06586617B1

Reaction notes

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