Diethyl Ether → 1-Isocyanatoheptadecane

HRID 647271Notes

Reaction equation

HRID 647271 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].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C([N:40]([CH2:43]C)CC)C.CC[O:47]CC>C1(C)C=CC=CC=1>[CH2:2]([N:40]=[C:43]=[O:47])[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

6

Reactant 4

HCID 3283Diethyl EtherHCID 5281Stearic AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 135601031-Isocyanatoheptadecane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 50 ml of toluene is dissolved 5.68 g of stearic acid, followed by addition of 5.5 g of diphenyl phosphororazidate ##STR19## hereinafter DPPA] and 3.0 ml of triethylamine. The mixture is stirred at room temperature for 2 hours. The reaction mixture is cooled, 100 ml of ether is added and the ether layer is washed with ice-water. The organic layer is taken, dehydrated with a dehydrating agent and refluxed for 2 hours, whereby 5.3 g of the above-indicated compound is obtained as colorless oil.

Workup

  1. temperatureThe reaction mixture is cooled
  2. washthe ether layer is washed with ice-water
  3. temperaturerefluxed for 2 hours

Sources & evidence

ORD record
ord-b75a4eae9b9b42a0848e379f272fe1c3
Source dataset
uspto-grants-1983_10
Patent number
US04408052

Reaction notes

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