2-Methylbenzenesulfonic acid → HCID 20551711, compound

HRID 1446957Notes

Reaction equation

HRID 1446957 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-4a4dd4ba6c164ea1a20c12111b79d810
Source dataset
uspto-grants-1982_02
Patent number
US04314840

Reaction notes

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