2-Methylbenzenesulfonic acid → HCID 20307437, compound

HRID 1763778Notes

Reaction equation

HRID 1763778 reaction equation
[CH2:1]([N:4]([CH2:9][CH:10]([O:13][CH3:14])[O:11][CH3:12])[C:5](=[O:8])[CH2:6][Cl:7])[C:2]#[CH:3].C1(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][CH2:12][CH2:14][O:13]1)[C:5](=[O:8])[CH2:6][Cl:7])[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 10340Sodium CarbonateHCID 20307409HCID 20307409, compound

Product 1

HCID 20307437HCID 20307437, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-Propargyl-N-(2,2-dimethoxyethyl)-α-chloroacetamide (8.5 grams), ethandiol-1,2 (2.16 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 160° to 165° 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-9a5c7a12461a462ca56932389872f23b
Source dataset
uspto-grants-1978_09
Patent number
US04113464

Reaction notes

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