Carbamate → Octyl isocyanate

HRID 488196Notes

Reaction equation

HRID 488196 reaction equation
[CH2:1]([NH2:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(CC)CC)C.C1(C2C=CC=CC=2)C=CC=CC=1.[C:29](=O)=[O:30].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(=O)([O-])N>C(#N)C>[CH2:1]([N:9]=[C:29]=[O:30])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 6

HCID 276CarbamateHCID 280Carbon Dioxide2×HCID 7095BiphenylHCID 8143OctylamineHCID 8471TriethylamineHCID 14812Phosphorus oxide (P4O10)3×

Product 1

HCID 76616Octyl isocyanateYield 89%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A Fischer-Porter bottle was charged with 0.65 g (5 mmol) of octyl amine, 1.17 g of P1 -tBu (5 mmol), 1.02 g (10 mmol) of triethylamine, 25 mL of acetonitrile and 154 mg (1 mmol) of biphenyl as an internal standard. The bottle was pressurized to 80 psig with carbon dioxide and the solution was stirred for 30 min. at room temperature. A second Fischer-Porter bottle was charged with 14.1 g (50 mmol) of phosphorus pentoxide, and 25 mL of acetonitrile then pressurized to 80 psig with CO2. The carbamate solution was added rapidly to the P2O5 suspension at room temperature causing some of the P2O5 to dissolve. An aliquot taken after three minutes gave a 89% yield of octyl isocyanate by G.C. analysis. The reaction was monitored for a total of 18 hrs during which time the yield of octyl isocyanate increased to a maximum of 97% (2.5 hr).

Workup

  1. dissolutionto dissolve
  2. waitAn aliquot taken after three minutes

Sources & evidence

ORD record
ord-fac430d1f6644f61b5c5800d2b4f87a5
Source dataset
uspto-grants-1994_03
Patent number
US05298651

Reaction notes

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