Dimethylcarbamoyl Chloride → HCID 53919230, compound

HRID 1578602Notes

Reaction equation

HRID 1578602 reaction equation
[CH3:1][O:2][NH:3][C:4](=[O:7])[CH2:5][Cl:6].C(N(CC)CC)C.[CH3:15][N:16]([CH3:20])[C:17](Cl)=[O:18]>C1C=CC=CC=1>[Cl:6][CH2:5][C:4]([O:7][C:17](=[O:18])[N:16]([CH3:20])[CH3:15])=[N:3][O:2][CH3:1]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 127743452-chloro-N-methoxyacetamide

Product 1

HCID 53919230HCID 53919230, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

N-Methoxychloroacetamide (12.3 grams; 0.1 mole), benzene (75 ml) and triethylamine (12 grams; 1.2 mole) are charged into a glass reaction flask equipped with a mechanical stirrer, therometer and reflux condenser. N,N-Dimethylcarbamoyl chloride (11 grams; 0.1 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,N-dimethylcarbamoyloxy)-2-methoxyiminoethane.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturetherometer 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-447edee53215470a9772400a320b0178
Source dataset
uspto-grants-1976_02
Patent number
US03937824

Reaction notes

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