Carbonyl Sulfide → Cyclohexyl isothiocyanate

HRID 1606593Notes

Reaction equation

HRID 1606593 reaction equation
[N+:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)([O-])=O.[C:10](=[S:12])=O>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[CH:4]1([N:1]=[C:10]=[S:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 10039Carbonyl SulfideHCID 14285Nitrocyclohexane2×

Product 1

HCID 14289Cyclohexyl isothiocyanateYield 1.3%

Reagents, catalysts & solvents 1

HCID 98885Molybdenum carbonyl (Mo(CO)6)Catalyst

Conditions

Temperature
150 °C

Procedure

Nitrocyclohexane (0.02 mole) and molybdenum hexacarbonyl (0.0002 mole) were placed in a 100 ml. rocking autoclave which was then sealed. Carbonyl sulfide (10.0 g., 0.16 mole) was charged to the autoclave from a small stainless steel cylinder, in which it was contained in the liquified state under its own vapor pressure (about 160 psig). The autoclave was then heated at 150°C. for 3 hours, after which it was cooled to ambient temperature, vented and opened. The reaction mixture was rinsed from the autoclave with 10 ml. of chloroform. The chloroform solution was separated from an insoluble residue by filtration, following which the solvent was evaporated to give 0.97 g. of product mixture. Vapor phase chromatographic analysis of this mixture showed it to contain 1.0% of nitrocyclohexane and 3.6% of cyclohexyl isothiocyanate (1.3% yield based on unrecovered nitrocyclohexane).

Workup

  1. customrocking autoclave which was then sealed
  2. temperatureafter which it was cooled to ambient temperature
  3. washThe reaction mixture was rinsed from the autoclave with 10 ml
  4. customThe chloroform solution was separated from an insoluble residue by filtration
  5. customwas evaporated
  6. customto give 0.97 g

Sources & evidence

ORD record
ord-d7eb1f368b9d4a1290386d68ec3c272c
Source dataset
uspto-grants-1976_04
Patent number
US03953488

Reaction notes

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