Methyl iodide → HCID 5031172, compound

HRID 1109745Notes

Reaction equation

HRID 1109745 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[CH:4][CH:3]=1.[N:11]#[C:12][NH2:13].[Na].[CH3:15]I>C(O)C>[C:12]([NH:13][C:9](=[N:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[S:10][CH3:15])#[N:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 164804-Chlorophenyl isothiocyanateHCID 57375518Cyanamidnatrium

Product 1

HCID 5031172HCID 5031172, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

p-Chlorophenyl isothiocyanate (XXXIa) (50.7 grams) is added to a suspension of sodium cyanamide (19.2 g) in ethanol (30 mL) with stirring which slowly dissolves and precipitates the sodium salt of N-cyano-N'-p-chlorophenylthiourea (XXXIIa) which is filtered off, washed with ethanol and dried to yield 36.2 grams which are suspended in 200 mL of ethanol and combined with 37.6 grams of methyl iodide with rapid stirring at ambient room temperature. The product separates as heat is evolved. The suspension is cooled in an ice bath, the solids filtered, washed with water and dried to give N-cyano-N'-p-chlorophenyl-S-methylisothiourea (XXXIIIa).

Workup

  1. dissolutionslowly dissolves
  2. customprecipitates the sodium salt of N-cyano-N'-p-chlorophenylthiourea (XXXIIa) which
  3. filtrationis filtered off
  4. washwashed with ethanol
  5. customdried
  6. customto yield 36.2 grams which
  7. stirringwith rapid stirring at ambient room temperature
  8. temperatureas heat
  9. temperatureThe suspension is cooled in an ice bath
  10. filtrationthe solids filtered
  11. washwashed with water
  12. customdried

Sources & evidence

ORD record
ord-0278f4546cd043d7b996b32701729535
Source dataset
uspto-grants-1994_06
Patent number
US05322858

Reaction notes

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