2-Chloroethyl isocyanate → HCID 131710029, compound

HRID 1578596Notes

Reaction equation

HRID 1578596 reaction equation
[CH2:1]([O:7][NH:8][C:9](=[O:12])[CH2:10][Cl:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cl:13][CH2:14][CH2:15][N:16]=[C:17]=[O:18]>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C1C=CC=CC=1>[Cl:11][CH2:10][C:9]([O:12][C:17](=[O:18])[NH:16][CH2:15][CH2:14][Cl:13])=[N:8][O:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 21559530HCID 21559530, compound

Product 1

HCID 131710029HCID 131710029, compound

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 241BenzeneSolvent2×

Procedure

N-Hexyloxychloroacetamide (19 grams; 0.1 mole), benzene (100 ml) and dibutyltin dilaurate (1 drop) are charged into a glass reaction flask equipped with a mechanical stirrer, thermometer and reflux condenser. β-Chloroethylisocyanate (12.6 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 3 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-β-chloroethylcarbamoyloxy)-2-hexyloxyiminoethane.

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 3 hours
  7. distillationAfter this time the reaction mixture is distilled
  8. customto remove benzene

Sources & evidence

ORD record
ord-681ce428e26c46d292c12c2988907ea6
Source dataset
uspto-grants-1976_02
Patent number
US03937824

Reaction notes

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