2-chloro-N-methoxyacetamide → HCID 131710030, compound

HRID 1578600Notes

Reaction equation

HRID 1578600 reaction equation
[CH3:1][O:2][NH:3][C:4](=[O:7])[CH2:5][Cl:6].[CH2:8]([C:11]1[CH:12]=[C:13]([N:17]=[C:18]=[O:19])[CH:14]=[CH:15][CH:16]=1)[CH:9]=[CH2:10]>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C1C=CC=CC=1>[Cl:6][CH2:5][C:4]([O:7][C:18](=[O:19])[NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH2:8][CH:9]=[CH2:10])[CH:12]=1)=[N:3][O:2][CH3:1]

Participants

5

Reactant 2

HCID 127743452-chloro-N-methoxyacetamideHCID 20396652HCID 20396652, compound

Product 1

HCID 131710030HCID 131710030, compound

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 241BenzeneSolvent2×

Procedure

N-Methoxychloroacetamide (12.3 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. 3-Allylphenylisocyanate (16 grams; 0.1 mole) dissolved in benzene (30 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 2 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-3-allylphenylcarbamoyloxy)-2-methoxyiminoethane.

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

Sources & evidence

ORD record
ord-6dc0e4e66917490886229cb72ad63d8d
Source dataset
uspto-grants-1976_02
Patent number
US03937824

Reaction notes

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