Methane → HCID 54267929, compound

HRID 1439372Notes

Reaction equation

HRID 1439372 reaction equation
[C:1]1([N:7]=[C:8]=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:10]#[N:11].[K+].C>C(O)C.O>[C:1]1([N:7]([C:10]#[N:11])[CH:8]=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 297MethaneHCID 7673Phenyl IsothiocyanateHCID 9032Potassium Cyanide

Product 1

HCID 54267929HCID 54267929, compoundYield 78.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 13.5 g (0.1 mol) phenyl isothiocyanate and 6.5 g (0.1 mol) potassium cyanide in 100 ml ethanol and 40 ml water was stirred at about 25° C for 1 hour. The solution was then diluted with water, slurried with charcoal and filtered. The filtrate was acidified with concentrated hydrochloric acid. An oil was separated on acidification. The oil solidified on standing and the resulting solid was filtered. The solid was then recrystallized from benzene/hexane to give 12.8 g N-phenyl cyanothioformamide, as a orange solid melting at 73°-81° C.

Workup

  1. filtrationfiltered
  2. customAn oil was separated on acidification
  3. filtrationthe resulting solid was filtered
  4. customThe solid was then recrystallized from benzene/hexane

Sources & evidence

ORD record
ord-149a280b08e547e3a4820747160a1c79
Source dataset
uspto-grants-1977_11
Patent number
US04059590

Reaction notes

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