2-Methylbenzenesulfonic acid → HCID 20551711, compound

HRID 1732212Notes

Reaction equation

HRID 1732212 reaction equation
[CH3:1][O:2][CH:3]([O:10][CH3:11])[CH2:4][NH:5][C:6](=[O:9])[CH2:7][Cl:8].[CH2:12](O)CCO.C1(C)C(S(O)(=O)=O)=CC=CC=1>C(OCC)C>[O:10]1[CH2:11][CH2:12][CH2:1][O:2][CH:3]1[CH2:4][NH:5][C:6](=[O:9])[CH2:7][Cl:8]

Participants

5

Reactant 3

HCID 69252-Methylbenzenesulfonic acidHCID 104421,3-PropanediolHCID 193700222-Chloro-N-(2,2-dimethoxyethyl)acetamide

Product 1

HCID 20551711HCID 20551711, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

N-(2,2-Dimethoxyethyl)-2-chloroacetamide (18.2 grams; 0.1 mole), 1,3-propanediol (7.61 grams; 0.1 mole) and 10 drops of a solution of 1 gram of toluenesulfonic acid in 100 ml of diethyl ether were charged into a glass reaction vessel fitted with a mechanical stirrer, thermometer, distillation head and condenser. The mixture was stirred and heated at about 120° C. for a period of about 1 hour while byproduct methanol was distilled off. The mixture was cooled to room temperature, sodium carbonate (2 grams) was added, and the slurry stirred for a period of about 1 hour. The slurry was filtered and the filtrate was stripped of solvent by mild warming under reduced pressure to yield the desired product N-(1,3-dioxan-2-ylmethyl)-2-chloracetamide as a residue.

Workup

  1. customfitted with a mechanical stirrer
  2. distillationthermometer, distillation head and condenser
  3. distillationwas distilled off
  4. temperatureThe mixture was cooled to room temperature
  5. additionsodium carbonate (2 grams) was added
  6. stirringthe slurry stirred for a period of about 1 hour
  7. filtrationThe slurry was filtered
  8. temperatureby mild warming under reduced pressure

Sources & evidence

ORD record
ord-a58c561b77c54f21b4e6165ecfe2d137
Source dataset
uspto-grants-1980_12
Patent number
US04237056

Reaction notes

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