Phosgene → 1-Isocyanato-1,2,3,4-tetrahydronaphthalene

HRID 1606786Notes

Reaction equation

HRID 1606786 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH:5]1([NH2:15])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1>C1(C)C=CC=CC=1.C1C=CC=CC=1>[CH:5]1([N:15]=[C:1]=[O:2])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 180661,2,3,4-Tetrahydro-1-naphthylamine

Product 1

HCID 162172391-Isocyanato-1,2,3,4-tetrahydronaphthaleneYield 86.1%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

To a stirred solution of 242.4 grams (2.46 moles) of phosgene in 200 ml of toluene and 600 ml of benzene is slowly added a solution of 119.9 grams (0.814 mole) of 1,2,3,4-tetrahydro-1-naphthylamine, while maintaining the reaction temperature at 10°C. to 15°C. The mixture is stirred overnight at room temperature and then heated to reflux under a nitrogen atmosphere. After 4 hours reflux, most of the solvent is distilled from the reaction at atmospheric pressure. The residual solvent is evaporated at reduced pressure. The crude product is distilled to give 121.4 grams of product with boiling point 90°C. to 96°C. (0.3 mm).

Workup

  1. temperaturewhile maintaining the reaction temperature at 10°C. to 15°C
  2. temperatureheated
  3. temperatureto reflux under a nitrogen atmosphere
  4. temperatureAfter 4 hours reflux, most of the solvent
  5. distillationis distilled from the reaction at atmospheric pressure
  6. customThe residual solvent is evaporated at reduced pressure
  7. distillationThe crude product is distilled

Sources & evidence

ORD record
ord-07adf40355534905838fae9ab768024e
Source dataset
uspto-grants-1976_04
Patent number
US03953606

Reaction notes

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