Phosgene → 1-(Isocyanatomethyl)naphthalene

HRID 1249748Notes

Reaction equation

HRID 1249748 reaction equation
[C:1](Cl)(Cl)=[O:2].[C:5]1([CH2:15][NH2:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:5]1([CH2:15][N:16]=[C:1]=[O:2])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 83551-NaphthalenemethanamineHCID 8471Triethylamine

Product 1

HCID 132577501-(Isocyanatomethyl)naphthalene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of phosgene (20% in toluene, 5 ml) was diluted with toluene (10 ml). A mixture of 1-naphthalenemethylamine (500 μl, 3.41 mmol), triethylamine (0.95 ml, 6.82 mmol) in toluene (5 ml) was added dropwise. The reaction mixture was heated at reflux overnight. The mixture was cooled to room temperature, and the solvent was removed. The residue was stirred with ether (50 ml) for 10 minutes and filtered. The filtrate was concentrated to give the crude product which was purified by flash chromatography (silica gel, methylene chloride) to give the desired product (518 mg) as a colorless oil. IR 2260 cm−1.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux overnight
  4. customthe solvent was removed
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customto give the crude product which
  8. customwas purified by flash chromatography (silica gel, methylene chloride)

Sources & evidence

ORD record
ord-5ec6578faf5143d29020bceac4ae9cfe
Source dataset
uspto-grants-2002_01
Patent number
US06335324B1

Reaction notes

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