Dimethyl Sulfate → N-carbomethoxy-S-methylisothiourea

HRID 2399030Notes

Reaction equation

HRID 2399030 reaction equation
S(OC)(O[CH3:5])(=O)=O.[NH2:8][C:9]([NH2:11])=[S:10].Cl[C:13]([O:15][CH3:16])=[O:14].[OH-].[Na+]>C(Cl)Cl.O>[CH3:16][O:15][C:13]([NH:8][C:9](=[NH:11])[S:10][CH3:5])=[O:14]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 2723790Thiourea

Product 1

HCID 145796808N-carbomethoxy-S-methylisothiourea

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

5 ml. of water and 1.9 ml. of dimethyl sulfate were added to 1.52 g. of thiourea (20 mmol). The mixture was stirred for about 3 mins. (until the initial heat evolution had subsided). The clear solution was then heated on a steam bath for 1 hour with stirring. The solution was cooled to about 20° C. and surrounded by a water bath (18° -22° C.). Freshly distilled methyl chloroformate (3.1 ml., 40 mmol) was added all at once followed by dropwise addition of 25 ml. of 10% aqueous sodium hydroxide over a period of 30 mins. The resulting product was isolated by extraction with methylene chloride and concentrated in vacuo to give an oily yellow solid which crystallized from ether as white prisms, mp. 97° -100° C.

Workup

  1. temperature(until the initial heat evolution
  2. temperatureThe clear solution was then heated on a steam bath for 1 hour
  3. stirringwith stirring
  4. customsurrounded by a water bath
  5. custom(18° -22° C.)
  6. additionall at once followed by dropwise addition of 25 ml
  7. concentrationconcentrated in vacuo
  8. customto give an oily yellow solid which
  9. customcrystallized from ether as white prisms, mp. 97° -100° C.

Sources & evidence

ORD record
ord-2a807b1f65124531a9a797e09ededed7
Source dataset
uspto-grants-1977_05
Patent number
US04026936

Reaction notes

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