Dimethyl Sulfate → HCID 178503891, compound

HRID 2352648Notes

Reaction equation

HRID 2352648 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[S:11])=[CH:5][CH:4]=1)#[N:2].[N:12]#[C:13][NH2:14].[Na].S(OC)(O[CH3:20])(=O)=O>C(O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[N:12][C:13]#[N:14])[S:11][CH3:20])=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 17626Benzonitrile, 4-isothiocyanato-HCID 57375518Cyanamidnatrium

Product 1

HCID 178503891HCID 178503891, compoundYield 151.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 32 g (0.1 mol) of 4-cyanophenyl isothiocyanate and of 12.8 g (0.2 mol) of monosodium cyanamide in 100 cm3 of absolute ethanol is maintained for 2 hours at boiling point. After cooling, the precipitate obtained is filtered and washed with 200 cm3 of absolute ethanol. The solid is then placed in suspension in a solution of dimethyl sulfate (25 g, 0.2 mol) in 500 cm3 of ethanol; the mixture is heated for two hours at boiling point. The final precipitate is filtered, washed with 2×100 cm3 of water and with 2×100 cm3 of ethanol, then is dried in vacuo. 32.8 g (yield 70%) of N-(4-cyanophenyl)-N'-cyano-S-methylisothiourea are obtained: ##STR9## which is a white solid, whose melting point is 225°-230° C.

Workup

  1. temperatureAfter cooling
  2. customthe precipitate obtained
  3. filtrationis filtered
  4. washwashed with 200 cm3 of absolute ethanol
  5. temperaturethe mixture is heated for two hours
  6. filtrationThe final precipitate is filtered
  7. washwashed with 2×100 cm3 of water and with 2×100 cm3 of ethanol
  8. customis dried in vacuo

Sources & evidence

ORD record
ord-a6efe3055e7c44e3b93f2a9ef2b89972
Source dataset
uspto-grants-1989_10
Patent number
US04877895

Reaction notes

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