Chloroform → HCID 136026279, compound

HRID 904699Notes

Reaction equation

HRID 904699 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2]([O:4][CH2:5][CH3:6])=O.[C:11]([C:14]1[CH:15]=[C:16]2[C:21](=CC=1O)[N:20]=[C:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[NH:18][C:17]2=[O:30])(=[O:13])[CH3:12].[O-]CC.[Na+].C(Cl)(Cl)Cl>C(O)C.Cl.O>[O:30]=[C:17]1[C:16]2[C:21](=[CH:6][C:5]3[O:4][C:2]([C:1]([O:8][CH2:9][CH3:10])=[O:7])=[CH:12][C:11](=[O:13])[C:14]=3[CH:15]=2)[N:20]=[C:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[NH:18]1

Participants

8

Reactant 4

HCID 6212ChloroformHCID 7268Diethyl OxalateHCID 2723922Sodium ethoxideHCID 135773206HCID 135773206, compound

Product 1

HCID 136026279HCID 136026279, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

A mixture of diethyl oxalate (4.4 ml) and the product of step (a) (1.1 g; 3.98 mmole) in ethanol (50 ml) was added slowly to freshly prepared sodium ethoxide (0.68 g; 9.99 mmole) in ethanol (80 ml) to give instantly a yellow suspension. After the addition, the mixture was heated to reflux on the steambath for half an hour to give a brown suspension. The mixture was cooled and neutralised with dilute hydrochloric acid to give a bright orange precipitate. This was extraced into chloroform, dried and evaporated to give a bright orange solide. The solid was redissolved in ethanolic hydrogen chloride. The solution was heated to reflux on a steambath for 3 hours. The mixture was cooled and was treated with water. After concentration, this was extracted into chloroform. The organic extract was washed with water, dried and evaporated to give a brown solid (0.95 g, 73%) whose structure was confirmed by NMR and mass spectroscopy.

Workup

  1. customto give instantly a yellow suspension
  2. additionAfter the addition
  3. temperaturethe mixture was heated
  4. temperatureto reflux on the steambath for half an hour
  5. customto give a brown suspension
  6. temperatureThe mixture was cooled
  7. customto give a bright orange precipitate
  8. customdried
  9. customevaporated
  10. customto give a bright orange solide
  11. temperatureThe solution was heated
  12. temperatureto reflux on a steambath for 3 hours
  13. temperatureThe mixture was cooled
  14. concentrationAfter concentration
  15. extractionthis was extracted into chloroform
  16. extractionThe organic extract
  17. washwas washed with water
  18. customdried
  19. customevaporated

Sources & evidence

ORD record
ord-314eff955d9f442c95059921f1222531
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

Loading…