Hydrochloric Acid → HCID 21866758, compound

HRID 1796394Notes

Reaction equation

HRID 1796394 reaction equation
[C:1]1([C:6]([NH:8][CH2:9][C:10]([O-:12])=O)=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1.[Na+].[CH2:14](O)C.O.Cl>N1C=CC=C(C)C=1.C(OC(=O)C)(=O)C>[C:1]1([C:6]([NH:8][CH2:9][C:10](=[O:12])[CH3:14])=[O:7])[S:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 23706078HCID 23706078, compound

Product 1

HCID 21866758HCID 21866758, compound

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 79703-MethylpyridineSolvent

Procedure

To 44.0 ml of a suspension of 16.70 g of sodium 2-(2-thenoylamino)acetate in β-picoline, 42.7 ml of acetic anhydride was added, and stirred for 3 hours at room temperature. After ice-cooling, 26.3 ml of ethanol, 129.7 ml of water and 45.2 ml of conc. hydrochloric acid were slowly added dropwise in sequence, and the mixture was stirred for 15 minutes as it is. After removal of ice-bath, the mixture was stirred for another 15 minutes at room temperature. Water (250 ml) was added and the precipitated crystals were collected, and washed with water. To the crystals was added 37.0 ml of water, and the mixture was heated to reflux for 1 hour. After 14.0 g of sodium chloride was added, the mixture was heated to reflux for another 1 hour. The reaction solution was extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. After addition of activated carbon (Kyoryoku-sirasagi® MOIWY433), the mixture was stirred for 30 minutes at room temperature. The solvent was distilled off under reduced pressure. The residue was crystallized by addition of t-butyl methyl ether to provide 7.15 g of the objective compound as pale brown crystals.

Workup

  1. temperatureAfter ice-cooling
  2. stirringthe mixture was stirred for 15 minutes as it
  3. customAfter removal of ice-bath
  4. stirringthe mixture was stirred for another 15 minutes at room temperature
  5. additionWater (250 ml) was added
  6. customthe precipitated crystals were collected
  7. washwashed with water
  8. additionTo the crystals was added 37.0 ml of water
  9. temperaturethe mixture was heated
  10. temperatureto reflux for 1 hour
  11. additionAfter 14.0 g of sodium chloride was added
  12. temperaturethe mixture was heated
  13. temperatureto reflux for another 1 hour
  14. extractionThe reaction solution was extracted with ethyl acetate
  15. dry with materialdried over anhydrous magnesium sulfate
  16. additionAfter addition of activated carbon (Kyoryoku-sirasagi® MOIWY433)
  17. stirringthe mixture was stirred for 30 minutes at room temperature
  18. distillationThe solvent was distilled off under reduced pressure
  19. customThe residue was crystallized by addition of t-butyl methyl ether

Sources & evidence

ORD record
ord-b85ed5dd294f4b6dbff9bb25ff50acf4
Source dataset
uspto-grants-2006_04
Patent number
US07030143B2

Reaction notes

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