Phosgene → (s)-Tetrahydrofurfurylisocyanate

HRID 2229416Notes

Reaction equation

HRID 2229416 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH2:5]([NH2:11])[C@H:6]1[O:10][CH2:9][CH2:8][CH2:7]1.C(N(CC)CC)C>C1(C)C=CC=CC=1.ClCCl>[CH2:5]([N:11]=[C:1]=[O:2])[C@H:6]1[O:10][CH2:9][CH2:8][CH2:7]1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 641530(S)-(+)-Tetrahydrofurfurylamine

Product 1

HCID 42182038(s)-Tetrahydrofurfurylisocyanate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of phosgene (2 mL of a ˜20% in toluene, 4.44 mmol) in 5 mL of dichloromethane at 0° C. was added a solution of (S)-tetrahydrofurfurylamine (0.15 mL, 1.48 mmol) and triethylamine (0.45 mL, 3.26 mmol) in 4 mL of dichloromethane dropwise over 20 min. The reaction mixture was stirred for 2.5 h at room temperature. The solvent was removed under reduced pressure, and the resulting residue was dissolved in ether. The triethylamine hydrochloride salt was removed by filtration. Concentration afforded 46A as a clear oil in quantitative yield.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe resulting residue was dissolved in ether
  3. customThe triethylamine hydrochloride salt was removed by filtration
  4. concentrationConcentration

Sources & evidence

ORD record
ord-8b7893b6aef44705b67229b1d84b9580
Source dataset
uspto-grants-2002_07
Patent number
US06420403B1

Reaction notes

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