Acetic Acid → HCID 178527928, compound

HRID 431496Notes

Reaction equation

HRID 431496 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=O)[C:2]1=O.[NH2:12][NH:13][C:14]([NH2:16])=[S:15].C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>O>[NH:16]1[C:2]2[NH:1][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]=2[N:12]=[N:13][C:14]1=[S:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7054IsatinHCID 11430Potassium CarbonateHCID 2723789Thiosemicarbazide

Product 1

HCID 178527928HCID 178527928, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of indole-2,3-dione 14b (74 mmol, 1 equiv.) in water (600 mL) is added thiosemicarbazide 14a (81.4 mmol, 1.1 equiv.) and potassium carbonate (11 mmol, 1.5 equiv.) as disclosed in Gladych, J. M. Z.; Hornby, R.; Hunt, J. H.; Jack, D.; Boyle, J. J.; Ferlauto, R. J.; Haff, R. F.; Kornendy, C. G; Standfield, F. J.; Stewart, R. C. J. Med. Chem. 1972, 15, 277-281 and references cited therein. The solution is stirred and refluxed for 7 hours. The red-orange solution is allowed to cool to room temperature overnight. The solution is acidified with acetic acid, and a yellow precipitate forms. The precipitate is filtered and washed with water, and dried under vacuum for 15 hours to yield 1,9-Dihydro-1,3,4,9-tetraaza-fluorene-2-thione 14c as a yellow powder.

Workup

  1. temperaturerefluxed for 7 hours
  2. filtrationThe precipitate is filtered
  3. washwashed with water
  4. customdried under vacuum for 15 hours

Sources & evidence

ORD record
ord-7765abc9ed9f468594de6940d5dc1b83
Source dataset
uspto-grants-2003_12
Patent number
US06660737B2

Reaction notes

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