Carbon Disulfide → HCID 20362127, compound

HRID 1679247Notes

Reaction equation

HRID 1679247 reaction equation
[C:1]([NH:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1)(=[O:3])[CH3:2].C([O-])(=O)C.[K+].[C:18](=[S:20])=[S:19].[CH2:21](Cl)[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:23]>CO>[C:1]([NH:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:22]([OH:23])([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:21][S:19][C:18]2=[S:20])=[CH:8][CH:7]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 107572-ChloroacetophenoneHCID 81068Acetic acid, 2-(4-aminophenyl)hydrazideHCID 517044Potassium Acetate

Product 1

HCID 20362127HCID 20362127, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

1-Acetyl-2-(4-aminophenyl)hydrazine (8.25 g., 0.05 mole) was added to a solution of potassium acetate (4.9 g., 0.05 mole) in methanol (50 ml). The temperature was maintained below 10° C throughout the remainder of the reaction. Carbon disulfide (3.8 g., 0.05 mole) mixed with methanol (5 ml) was added dropwise to the stirred suspension which was stirred for one hour. Phenacyl chloride (3.9 g., 0.02 mole) dissolved in methanol (15 ml) was added dropwise with stirring and the reaction mixture stirred for one and one-half hours. The resulting solution was allowed to warm to room temperature; most of the methanol was removed under vacuum. The solution was diluted with water. The product separated out as a white gummy material which crystallized on stirring and chilling. The white solid was collected by filtration, washed with water, and allowed to dry at room temperature. Yield 8.7 g (97%), m.p. 80°-84° C.

Workup

  1. temperatureThe temperature was maintained below 10° C throughout the remainder of the reaction
  2. additionwas added dropwise to the stirred suspension which
  3. additionwas added dropwise
  4. stirringwith stirring
  5. stirringthe reaction mixture stirred for one and one-half hours
  6. custommost of the methanol was removed under vacuum
  7. additionThe solution was diluted with water
  8. customThe product separated out as a white gummy material which
  9. customcrystallized
  10. stirringon stirring
  11. temperaturechilling
  12. filtrationThe white solid was collected by filtration
  13. washwashed with water
  14. customto dry at room temperature

Sources & evidence

ORD record
ord-a71391cc6d464eb6ae9f1a2202042309
Source dataset
uspto-grants-1978_03
Patent number
US04080207

Reaction notes

Loading…