Ethanol → HCID 178517003, compound

HRID 2297863Notes

Reaction equation

HRID 2297863 reaction equation
C(O[CH:4]=[C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]3[N:16]=[CH:15][S:14][C:12]3=2)[NH:7][C:6]1=[O:17])C.[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:28][CH2:29][C:30]2[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(O)C>O>[O:17]=[C:6]1[C:5](=[CH:4][NH:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=3)(=[O:27])=[O:26])=[CH:21][CH:20]=2)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]3[N:16]=[CH:15][S:14][C:12]3=2)[NH:7]1

Participants

5

Reactant 3

HCID 702EthanolHCID 1133837HCID 1133837, compoundHCID 539908078-[Ethoxymethylidene]-6H-[1,3]thiazolo[5,4-e]indol-7-one

Product 1

HCID 178517003HCID 178517003, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 250-ml round bottom flask was added a magnetic stir bar, 8-[ethoxymethylidene]-6H-[1,3]thiazolo[5,4-e]indol-7-one (1.98 grams, 8.05 mmol), 4-amino-N-(4-pyridinylmethyl)benzenesulfonamide (2.16 grams, 8.2 mmol) and 95% ethanol (80 ml). The round bottom reaction flask was fitted with a water cooled reflux condenser. The reaction vessel was placed in an oil bath at room temperature with stirring and the temperature of the oil bath was then raised to a gentle reflux and maintained at that temperature for approximately 36 hours. The reaction vessel was removed from the oil bath and the hot mixture was filtered with the solids being collected by suction filtration. The resultant solid was washed with excess 95% ethanol and collected by suction filtration. The solid was then dried under vacuum for two days at room temperature to yield 2.785 grams (74.7%) of the thiazolindolinone compound. MS (M+H)=464.

Workup

  1. additionTo a 250-ml round bottom flask was added a magnetic stir bar
  2. temperaturecooled
  3. temperaturereflux condenser
  4. customThe reaction vessel was placed in an oil bath at room temperature
  5. temperaturethe temperature of the oil bath was then raised to
  6. temperaturea gentle reflux
  7. temperaturemaintained at that temperature for approximately 36 hours
  8. customThe reaction vessel was removed from the oil bath
  9. filtrationthe hot mixture was filtered with the solids
  10. filtrationbeing collected by suction filtration
  11. washThe resultant solid was washed with excess 95% ethanol
  12. filtrationcollected by suction filtration
  13. customThe solid was then dried under vacuum for two days at room temperature

Sources & evidence

ORD record
ord-3c8c66e556494605906665155713b3c3
Source dataset
uspto-grants-2002_12
Patent number
US06492398B1

Reaction notes

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