Acetone → Nonyl isocyanate

HRID 229308Notes

Reaction equation

HRID 229308 reaction equation
C(Cl)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[N-]=[N+]=[N-].[Na+].[N-:17]=[N+]=[N-].C1(C)C=CC=CC=1.C[C:28](C)=[O:29]>O>[CH2:2]([N:17]=[C:28]=[O:29])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 5

HCID 180AcetoneHCID 1140TolueneHCID 33557Sodium AzideHCID 33558AzideHCID 66982Decanoyl chloride

Product 1

HCID 11275250Nonyl isocyanateYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

A solution of decanoyl chloride (20 g, 104.8 mmoles) in acetone (30 ml) was dropped into a solution of sodium azide (9.53 g, 146.6 mmoles) in water (30 ml), cooled in an ice bath. The temperature of the azide solution was kept between 10 and 15° C. after one hour, the solution was transferred in a separatory funnel and the lower phase (the aqueous one) was eliminated. The higher phase was transferred into a flask containing 100 ml of toluene, previously warmed at 65° C. After 1.5 hours, the solution was evaporated to dryness, giving 13.37 g crude product, which after vacuum distillation gave 8.3 g pure product in the form of colourless liquid.

Workup

  1. temperaturecooled in an ice bath
  2. customthe solution was transferred in a separatory funnel
  3. customThe higher phase was transferred into a flask
  4. customthe solution was evaporated to dryness
  5. customgiving 13.37 g crude product, which
  6. distillationafter vacuum distillation

Sources & evidence

ORD record
ord-e631cfe1ea7f4dc9b17ed5ccc3636e9b
Source dataset
uspto-grants-2009_07
Patent number
USRE040861E1

Reaction notes

Loading…