Methyl iodide → HCID 178503888, compound

HRID 1649861Notes

Reaction equation

HRID 1649861 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[S:10])[CH:5]=[CH:6][CH:7]=1.[N:11]#[C:12][NH2:13].[Na].[CH3:15]I>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[N:11][C:12]#[N:13])[S:10][CH3:15])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 754493-Chlorophenyl isothiocyanateHCID 57375518Cyanamidnatrium

Product 1

HCID 178503888HCID 178503888, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Ten grams (59 mmol) of 3-chlorophenyl isothiocyanate and 4.15 g (65 mmol) of monosodium cyanamide are mixed in 100 cm3 of absolute ethanol and kept boiling for 2 hours. After elimination of the solvent, the resulting solid residue is washed with 100 cm3 of ethyl ether. The compound is then suspended in a solution of 4.8 cm3 (77 mmol) of methyl iodide in 50 cm3 of ethanol. The mixture is then left at ambient temperature for 20 hours. The final precipitate is filtered and washed with water (2×50 cm3) and ethanol (2×50 cm3) and is then dried in vacuo. A 10.1 gram portion of N-(3-chlorophenyl)-N'-cyano-S-methylisothiourea is obtained with a melting point of 167° C. ##STR88##

Workup

  1. washAfter elimination of the solvent, the resulting solid residue is washed with 100 cm3 of ethyl ether
  2. waitThe mixture is then left at ambient temperature for 20 hours
  3. filtrationThe final precipitate is filtered
  4. washwashed with water (2×50 cm3) and ethanol (2×50 cm3)
  5. customis then dried in vacuo

Sources & evidence

ORD record
ord-98c6f286760b4e9ea5417898df592680
Source dataset
uspto-grants-1990_05
Patent number
US04921939

Reaction notes

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