2-Methylbenzenesulfonic acid → HCID 20307437, compound

HRID 1763779Notes

Reaction equation

HRID 1763779 reaction equation
[CH:1]([N:4]([CH2:9][CH:10]([O:14][CH2:15][CH3:16])[O:11]CC)[C:5](=[O:8])[CH2:6][Cl:7])([CH3:3])C.[C:17]1(C)C(S(O)(=O)=O)=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH2:1]([N:4]([CH2:9][CH:10]1[O:11][CH2:16][CH2:15][O:14]1)[C:5](=[O:8])[CH2:6][Cl:7])[C:3]#[CH:17]

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 10340Sodium CarbonateHCID 22768137HCID 22768137, compound

Product 1

HCID 20307437HCID 20307437, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Isopropyl-N-(2,2-diethoxyethyl)-α-chloroacetamide (10 grams), propandiol-1,2 (2.9 ml) and trace amounts of toluenesulfonic acid were charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture was heated at reflux until no more ethanol was given off. After this time sodium carbonate (1 gram) was added to the mixture with stirring and the resulting mixture was distilled to yield the desired product N-propargyl-N-(1,3-dioxolan-2-ylmethyl)-α-chloroacetamide having a boiling point of 155° to 160° C. at 1 mm of Hg pressure.

Workup

  1. additionwere charged into a glass reaction vessel
  2. customequipped with a mechanical stirrer
  3. temperaturethermometer and reflux condenser
  4. temperatureThe reaction mixture was heated
  5. distillationthe resulting mixture was distilled

Sources & evidence

ORD record
ord-f86cc91f40b54bfe98080f31b3dd564c
Source dataset
uspto-grants-1978_09
Patent number
US04113464

Reaction notes

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