Diethyl Oxalate → HCID 826698, compound

HRID 1075020Notes

Reaction equation

HRID 1075020 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[S:5][C:4]2[CH:13]=[C:14](CC(N)=O)[CH:15]=[CH:16][C:3]1=2.C(OC(=O)C(OCC)=O)C.CC(C)([O-])C.[K+]>CN(C)C=O>[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[S:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 20270231HCID 20270231, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 826698HCID 826698, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Stir at room temperature a mixture of 5.118 gm. of the amide of Step 5, 2.939 gm. of diethyloxalate, 4.723 gm. of potassium t-butoxide and 40 ml. of dimethylformamide for 6 hours. Pour the reaction mixture into 300 ml. of ice-water and extract with 300 ml. of ethyl acetate. Acidify with 6N hydrochloric acid and separate the ethyl acetate layer. Wash with saturated sodium chloride solution and dry. Evaporate to dryness and dissolve the residue in warm dioxane. Treat with a slight excess of ammonia and separate the solid by filtration. Wash with dioxane and dry. Suspend the product in water, acidify with 6N hydrochloric acid and extract with ethyl acetate. Wash the extract with saturated sodium chloride solution, dry over magnesium sulfate and evaporate to obtain the title product.

Workup

  1. additiona mixture of 5.118 gm
  2. additionPour the reaction mixture into 300 ml
  3. extractionof ice-water and extract with 300 ml
  4. customseparate the ethyl acetate layer
  5. washWash with saturated sodium chloride solution
  6. customdry
  7. customEvaporate to dryness
  8. dissolutiondissolve the residue in warm dioxane
  9. additionTreat with a slight excess of ammonia
  10. customseparate the solid
  11. filtrationby filtration
  12. washWash with dioxane
  13. customdry
  14. extractionextract with ethyl acetate
  15. washWash the
  16. extractionextract with saturated sodium chloride solution
  17. dry with materialdry over magnesium sulfate
  18. customevaporate

Sources & evidence

ORD record
ord-bdf9c207a2dc48b9914d444812ab2796
Source dataset
uspto-grants-1983_07
Patent number
US04394515

Reaction notes

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