Stearic Acid → 1-Isocyanatoheptadecane

HRID 974689Notes

Reaction equation

HRID 974689 reaction equation
C(O)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.C([N:40]([CH2:43]C)CC)C>C1C=CC=CC=1>[CH2:2]([N:40]=[C:43]=[O:28])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 5281Stearic AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 135601031-Isocyanatoheptadecane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 2.96 g of stearic acid, 1.87 ml of diphenylphosphoryl azide and 1.21 ml of triethylamine in 90 ml of benzene was heated under reflux for 16 hours. At the end of this time, the mixture was cooled and washed, in turn, with a saturated aqueous solution of sodium bicarbonate and with water. The mixture was then dried, and the solvent was evaporated off under reduced pressure, to give 2.40 g of crude heptadecyl isocyanate.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hours
  3. temperatureAt the end of this time, the mixture was cooled
  4. washwashed, in turn, with a saturated aqueous solution of sodium bicarbonate and with water
  5. customThe mixture was then dried
  6. customthe solvent was evaporated off under reduced pressure

Sources & evidence

ORD record
ord-71c5fce2a04b40a2a0ebfc74ffda76d9
Source dataset
uspto-grants-1991_11
Patent number
US05068340

Reaction notes

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