Phenyl isocyanate → HCID 53872487, compound

HRID 1578592Notes

Reaction equation

HRID 1578592 reaction equation
[CH2:1]([O:4][NH:5][C:6](=[O:9])[CH2:7][Cl:8])[CH2:2][CH3:3].[C:10]1([N:16]=[C:17]=[O:18])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C1C=CC=CC=1>[Cl:8][CH2:7][C:6]([O:9][C:17](=[O:18])[NH:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[N:5][O:4][CH2:1][CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 21559531HCID 21559531, compound

Product 1

HCID 53872487HCID 53872487, compound

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 241BenzeneSolvent2×

Procedure

N-Propoxychloroacetamide (15.1 grams; 0.1 mole), benzene (80 ml) and dibutyltin dilaurate (1 drop) are charged into a glass reaction flask equipped with a mechanical stirrer, thermometer and reflux condenser. Phenylisocyanate (12.1 grams; 0.12 mole) dissolved in benzene (25 ml) is incrementally added to the reaction mixture, with stirring, at room temperature. After the addition is completed the reaction mixture is heated at reflux for a period of about 20 hours. After this time the reaction mixture is distilled to remove benzene and unreacted starting material thereby yielding the desired product 1-chloro-2-(N-phenylcarbamoyloxy)-2-propoxyiminoethane.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. additionis incrementally added to the reaction mixture
  4. additionAfter the addition
  5. temperatureis heated
  6. temperatureat reflux for a period of about 20 hours
  7. distillationAfter this time the reaction mixture is distilled
  8. customto remove benzene

Sources & evidence

ORD record
ord-8253c7783ff74e8cbfb6567d17d53996
Source dataset
uspto-grants-1976_02
Patent number
US03937824

Reaction notes

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