Ethanol → HCID 12832643, compound

HRID 703246Notes

Reaction equation

HRID 703246 reaction equation
[C:1]([NH:4][C:5]([C:7]([NH:9][C:10](=O)[CH3:11])=[O:8])=[O:6])(=O)[CH3:2].N1[CH:18]=[CH:17][CH:16]=CC=1.O.[CH:20](Cl)(Cl)Cl.[CH2:24](O)[CH3:25]>>[C:7]([N:9]1[CH2:16][CH2:17][CH2:18][CH2:11][CH2:10]1)(=[O:8])[C:5]([N:4]1[CH2:25][CH2:24][CH2:20][CH2:2][CH2:1]1)=[O:6]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 1049PyridineHCID 6212ChloroformHCID 3016168N,N'-Diacetyloxamide2×

Product 1

HCID 12832643HCID 12832643, compoundYield 39.2%

Procedure

A suspension of N,N'-diacetyloxamide (10 g, 0.058 mol) in ethyl alcohol (20 ml) is charged into a three-necked flask equipped with a reflux condenser, an inlet tube for nitrogen, a dropping funnel, and a magnetic stirrer. 98 % Pyridine (40 ml, 0.40 mol) is then dripped therein at 70° C., and after 40 minutes the complete solving of N,N'-diacetyloxamide in the reaction mixture is observed. The temperature is brought to 95° C. and kept at this value for 6.5 hours. Then water (60 ml) and chloroform (60 ml) are added to the reaction mixture and the organic phase is separated. Chloroform is distilled off and ethyl ether (30 ml) is added to precipitate the compound of the title. The precipitate is recovered by filtration and dried, thus affording the compound of the title (5.1 g, 0.023 mol, yield 39.2%) with m.p. 88°-90° C.

Workup

  1. additionis charged into a three-necked flask
  2. customequipped with a reflux condenser, an inlet tube for nitrogen, a dropping funnel, and a magnetic stirrer
  3. customis brought to 95° C.
  4. customthe organic phase is separated
  5. distillationChloroform is distilled off
  6. additionethyl ether (30 ml) is added
  7. customto precipitate the compound of the title
  8. filtrationThe precipitate is recovered by filtration
  9. customdried
  10. customthus affording the compound of the title (5.1 g, 0.023 mol, yield 39.2%) with m.p. 88°-90° C.

Sources & evidence

ORD record
ord-4d3599b3c7bd4f6f9a9e39fb515ac711
Source dataset
uspto-grants-1991_01
Patent number
US04981963

Reaction notes

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