Oxalic Acid → HCID 86746511, compound

HRID 1646926Notes

Reaction equation

HRID 1646926 reaction equation
Cl[C:2]1[C:3]([C:8]2(O)[CH2:13][CH2:12][CH2:11][N:10]([CH3:14])[CH2:9]2)=[N:4][CH:5]=[CH:6][N:7]=1.S(Cl)(Cl)=O.[C:20]([OH:25])(=[O:24])[C:21]([OH:23])=[O:22]>C(OCC)(=O)C>[C:20]([OH:25])(=[O:24])[C:21]([OH:23])=[O:22].[CH3:21][O:22][C:2]1[C:3]([C:8]2[CH2:9][N:10]([CH3:14])[CH2:11][CH2:12][CH:13]=2)=[N:4][CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 971Oxalic AcidHCID 24386Thionyl ChlorideHCID 10331340HCID 10331340, compound

Product 1

HCID 86746511HCID 86746511, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.32 g of (1) (0.0014 mol) and 10 ml of thionyl chloride was heated to reflux for 1.5 h. The excess thionyl chloride was evaporated, the residue treated with ice-water and made basic with saturated aqueous K2CO3. The mixture was extracted 3× with 25 ml of CH2Cl2, the extracts washed with brine, dried, and the solvent evaporated. The residue was dissolved in 5 ml of methanol and added to 25 ml of methanol that had reacted with 0.35 g of Na (0.015 mol). The reaction was heated to reflux for 1.5 h. The solvent was evaporated, the residue was treated with ice-water and the mixture extracted 3× with 25 ml of CH2Cl2. The extracts were washed with brine, dried, and the solvent evaporated to give a dark liquid, 0.15 g. The liquid was dissolved in ethyl acetate and treated with oxalic acid to give 0.05 g of (2) after recrystallization from ethyl acetate, mp 150°-151° C. NMR ppm (D2O) 2.6-2.9 (2H, m), 3.1 (3H, s), 3.3 (1H, m), 3.65 (1H, m), 4.0 (3H, s), 4.05 (1H, dd), 4.35 (1H, d), 6.95 (1H, bs), 8.07 (1H, d), 8.1 (1H, d). Anal. C11H15N3O-C2H2O4 requires C: 52.88; H: 5.80; N: 14.23%. Found C: 52.66; H: 5.94; N: 14.04%.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1.5 h
  3. customThe excess thionyl chloride was evaporated
  4. additionthe residue treated with ice-water
  5. extractionThe mixture was extracted 3× with 25 ml of CH2Cl2
  6. washthe extracts washed with brine
  7. customdried
  8. customthe solvent evaporated
  9. dissolutionThe residue was dissolved in 5 ml of methanol
  10. additionadded to 25 ml of methanol that
  11. temperatureThe reaction was heated
  12. temperatureto reflux for 1.5 h
  13. customThe solvent was evaporated
  14. additionthe residue was treated with ice-water
  15. extractionthe mixture extracted 3× with 25 ml of CH2Cl2
  16. washThe extracts were washed with brine
  17. customdried
  18. customthe solvent evaporated
  19. customto give a dark liquid, 0.15 g

Sources & evidence

ORD record
ord-d6f9c5c2039a458bb05373a66ac7519c
Source dataset
uspto-grants-1993_01
Patent number
US05182283

Reaction notes

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