Sodium Carbonate → 3-[4-(2-Acetylhydrazino)phenyl]rhodanine

HRID 1679244

Reaction equation

HRID 1679244 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].C(CS[C:12](=[S:18])[S:13][CH2:14][C:15]([OH:17])=O)(O)=O.[C:19]([NH:22][NH:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][CH:25]=1)(=[O:21])[CH3:20]>O>[C:19]([NH:22][NH:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:15](=[O:17])[CH2:14][S:13][C:12]2=[S:18])=[CH:26][CH:25]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 806183,5-Dithia-4-thioxo-1,7-heptanedioic acidHCID 81068Acetic acid, 2-(4-aminophenyl)hydrazide

Product 1

HCID 203621233-[4-(2-Acetylhydrazino)phenyl]rhodanine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium carbonate (1.06g. 0.010 mole) was dissolved in water (100 ml). Bis(carboxymethyl)trithiocarbonate (4.52g, 0.02 mole) was added portionwise with vigorous stirring. When solution was complete, the reaction mixture was warmed to 80°-85° C and 1-acetyl-2-(4-aminophenyl)hydrazine (3.30 g, 0.020 moles) was added in one portion. The reaction mixture was heated with stirring for 11/2 hours, cooled to about 50°-60° C, then reheated at 80°-85° C. The product began to precipitate during reheating. After another 2 hours of heating the mixture was cooled to room temperature, chilled and filtered. The solid which was collected was washed with water and dried. Yield 2.95g (53%), mp 210°-213° C (dec).

Workup

  1. temperaturethe reaction mixture was warmed to 80°-85° C
  2. temperatureThe reaction mixture was heated
  3. temperaturecooled to about 50°-60° C
  4. customreheated at 80°-85° C
  5. customto precipitate
  6. temperatureAfter another 2 hours of heating the mixture
  7. temperaturechilled
  8. filtrationfiltered
  9. customThe solid which was collected
  10. washwas washed with water
  11. customdried

Sources & evidence

ORD record
ord-6aac6c739c0742c7af0af338a0779eee
Source dataset
uspto-grants-1978_03
Patent number
US04080207

Linked notes

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