Ethanol → HCID 178517000, compound

HRID 840816

Reaction equation

HRID 840816 reaction equation
C(O[CH:4]=[C:5]1[C:16]2[C:8](=[CH:9][CH:10]=[C:11]3[C:15]=2[S:14][CH:13]=[N:12]3)[NH:7][C:6]1=[O:17])C.[CH:18]1[CH:19]=[CH:20][N:21]=[C:22]([NH:24][S:25]([C:28]2[CH:29]=[CH:30][C:31]([NH2:34])=[CH:32][CH:33]=2)(=[O:27])=[O:26])[CH:23]=1.C(O)C>O>[O:17]=[C:6]1[C:5](=[CH:4][NH:34][C:31]2[CH:30]=[CH:29][C:28]([S:25]([NH:24][C:22]3[CH:23]=[CH:18][CH:19]=[CH:20][N:21]=3)(=[O:27])=[O:26])=[CH:33][CH:32]=2)[C:16]2[C:8](=[CH:9][CH:10]=[C:11]3[C:15]=2[S:14][CH:13]=[N:12]3)[NH:7]1

Participants

5

Reactant 3

HCID 702EthanolHCID 5336SulfapyridineHCID 539908078-[Ethoxymethylidene]-6H-[1,3]thiazolo[5,4-e]indol-7-one

Product 1

HCID 178517000HCID 178517000, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 25 ml round bottom flask was added a stir bar, 246 mg (1.00 mmol) of 8-ethoxymethylene-6,8-dihydro-1-thia-3,6-diaza-as-indacen-7-one, 249 mg (1.00 mmol) of sulfapyridine and 10 ml of ethanol. The flask was fitted with a water-cooled reflux condenser, and the mixture was heated to reflux using an oil bath with stirring for 18 h. The reaction was allowed to cool and was filtered. The precipitate was washed with excess ethanol and dried under vacuum to yield 321 mg (71%) of the title compound: 1H NMR (DMSO-d6): δ11.9 (br s, 1H), 11.2 (d, 1H), 10.9 (s, 1H), 9.3 (s, 1H), 8.1 (d, 2H), 7.9 (m, 3H), 7.8 (m, 1H), 7.6 (d, 2H), 7.2 (d, 1H), 7.2 (d, 1H), 6.9 (t, 1H); C21H15N5O3S2: APCI−MS m/z 450 (M+H)+.

Workup

  1. additionTo a 25 ml round bottom flask was added a stir bar
  2. temperaturecooled
  3. temperaturereflux condenser
  4. temperaturethe mixture was heated
  5. temperatureto reflux
  6. temperatureto cool
  7. filtrationwas filtered
  8. washThe precipitate was washed with excess ethanol
  9. customdried under vacuum

Sources & evidence

ORD record
ord-37c63274ee1146ddb03ef24ca5e8c312
Source dataset
uspto-grants-2002_04
Patent number
US06369086B1

Linked notes

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