Isatin → 5H-[1,2,4]Triazino[5,6-b]indole-3-thiol

HRID 355367Notes

Reaction equation

HRID 355367 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=O.[NH2:12][NH:13][C:14]([NH2:16])=[S:15].C(=O)([O-])[O-].[K+].[K+]>O>[N:12]1[NH:13][C:14](=[S:15])[N:16]=[C:2]2[C:4]=1[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[NH:1]2

Participants

5

Reactant 3

HCID 7054IsatinHCID 11430Potassium CarbonateHCID 2723789Thiosemicarbazide

Product 1

HCID 1354038085H-[1,2,4]Triazino[5,6-b]indole-3-thiolYield 79.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7.36 g (50.0 mmoles) of isatin, 250 ml of water, 5.01 g (55.0 mmoles) of thiosemicarbazide and 10.4 g (75.0 mmoles) of potassium carbonate was heated to reflux. After 30 minutes, a red solution resulted which was cooled to room temperature and filtered through celite. The pH was adjusted to 4.5 with glacial acetic acid and the resulting yellow solid was collected and washed with hot ethanol. After drying, 8.04 g of material was obtained. (J. Medicinal Chemistry, 15:277 (1972))

Workup

  1. temperaturewas heated to reflux
  2. customa red solution resulted which
  3. filtrationfiltered through celite
  4. customthe resulting yellow solid was collected
  5. washwashed with hot ethanol
  6. customAfter drying

Sources & evidence

ORD record
ord-05e35cfca6064899b62c4ca600b8335e
Source dataset
uspto-grants-1998_11
Patent number
US05830894

Reaction notes

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