Carbon Disulfide → Cyclohexyl isothiocyanate

HRID 372176Notes

Reaction equation

HRID 372176 reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[C:10](=S)=[S:11].N#CCl>C(Cl)Cl.O>[CH:1]1([N:7]=[C:10]=[S:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 7965CyclohexylamineHCID 10477Cyanogen ChlorideHCID 14798Sodium Hydroxide2×

Product 1

HCID 14289Cyclohexyl isothiocyanateYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

In one hour 0.5 mole of cyclohexyl amine, 0.5 mole of sodium hydroxide and 60 grams of water were treated with 0.5 mole of carbon disulfide. The N-cyclohexyl sodium dithiocarbamate solution was stirred for a further hour at 50° C. There were added 1,000 cc of water, 20 grams of sodium hydroxide and 250 cc of methylene chloride. Under stirring there were led in at 6° C, 0.515 mol of cyanogen chloride. After the separation the methylene chloride layer was distilled. There were isolated 69.5 grams of cyclohexyl isothiocyanate (B.P. 98.5° C/13 mm Hg), corresponding to a yield of 98.4% of theory.

Workup

  1. customAfter the separation the methylene chloride layer
  2. distillationwas distilled

Sources & evidence

ORD record
ord-d6a598af94e84cc6928eafe395643e06
Source dataset
uspto-grants-1978_05
Patent number
US04089887

Reaction notes

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