Carbon Dioxide → HCID 18707339, compound

HRID 263589Notes

Reaction equation

HRID 263589 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([C:19]2[S:20][CH:21]=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][C:25]=3[OH:31])[N:23]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH3:18])[CH3:8].C(=O)=O>CC(C)=O>[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([C:19]2[S:20][CH:21]=[C:22]([C:24]3[C:25]([OH:31])=[CH:26][C:27]([OH:30])=[C:28]([C:1]([OH:2])=[O:4])[CH:29]=3)[N:23]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH3:18])[CH3:8]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 11430Potassium CarbonateHCID 18707286HCID 18707286, compound

Product 1

HCID 18707339HCID 18707339, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
-78 °C

Procedure

2 g of potassium carbonate was added to a solution of 1.5 g of 2-(3,4-diethoxyphenyl)-4-(2,4-dihydroxyphenyl)thiazole in 40 ml of acetone. Thereto was added 40 g of dry ice under cooling at -78° C. The mixture was sealed in a tube and stirred at 150° C. for 18 hours. The solvent was distilled off. The residue was made weakly acidic with 100 ml of ethyl acetate and 10% hydrochloric acid, and extraction and phase separation was conducted. The organic layer was washed with 30 ml of a saturated aqueous sodium chloride solution and dried. The solvent was distilled off. The residue was mixed with 40 ml of dichloromethane. The insoluble was collected by filtration, washed with a small amount of dichloromethane, dried and recrystallized from ethyl acetate to obtain 241 mg of 2-(3,4-diethoxyphenyl)-4-(3-carboxy-4,6-dihydroxyphenyl)thiazole.

Workup

  1. customThe mixture was sealed in a tube
  2. distillationThe solvent was distilled off
  3. extractionThe residue was made weakly acidic with 100 ml of ethyl acetate and 10% hydrochloric acid, and extraction and phase separation
  4. washThe organic layer was washed with 30 ml of a saturated aqueous sodium chloride solution
  5. customdried
  6. distillationThe solvent was distilled off
  7. additionThe residue was mixed with 40 ml of dichloromethane
  8. filtrationThe insoluble was collected by filtration
  9. washwashed with a small amount of dichloromethane
  10. customdried
  11. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-689730b83f8e4b9aa681ce17174a10c1
Source dataset
uspto-grants-1997_07
Patent number
US05643932

Reaction notes

Loading…