Isopropyl isocyanate → 1-chloro-2-(N-isopropylcarbamoyloxy)-2-ethoxyiminoethane

HRID 1578591Notes

Reaction equation

HRID 1578591 reaction equation
[CH2:1]([O:3][NH:4][C:5](=[O:8])[CH2:6][Cl:7])[CH3:2].[CH:9]([N:12]=[C:13]=[O:14])([CH3:11])[CH3:10]>C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C1C=CC=CC=1>[Cl:7][CH2:6][C:5]([O:8][C:13](=[O:14])[NH:12][CH:9]([CH3:11])[CH3:10])=[N:4][O:3][CH2:1][CH3:2]

Participants

5

Reactant 2

HCID 61277Isopropyl isocyanateHCID 127743472-Chloro-N-ethoxyacetamide

Product 1

HCID 538275211-chloro-2-(N-isopropylcarbamoyloxy)-2-ethoxyiminoethane

Reagents, catalysts & solvents 2

HCID 9809426Di-n-butyldilauryltinCatalystHCID 241BenzeneSolvent2×

Procedure

N-Ethoxychloroacetamide (6.9 grams; 0.05 mole), benzene (70 ml) and dibutyltin dilaurate (1 drop) are charged into a glass reaction flask equipped with a mechanical stirrer, thermometer and reflux condenser. Isopropylisocyanate (5.1 grams; 0.06 mole) dissolved in benzene (20 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-isopropylcarbamoyloxy)-2-ethoxyiminoethane.

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-6114128ae4a44cc98a8a63468da45d73
Source dataset
uspto-grants-1976_02
Patent number
US03937824

Reaction notes

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