Carbon Disulfide → HCID 178514763, compound

HRID 255818Notes

Reaction equation

HRID 255818 reaction equation
[NH2:1][S:2]([CH2:5][C:6]1[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=1[C:8]([NH:10][NH2:11])=[O:9])(=[O:4])=[O:3].[OH-].[K+].[C:18](=S)=[S:19]>C(O)C.O>[SH:19][C:18]1[O:9][C:8]([C:7]2[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=2[CH2:5][S:2]([NH2:1])(=[O:3])=[O:4])=[N:10][N:11]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 139587751-[2-(Hydrazinecarbonyl)phenyl]methanesulfonamide

Product 1

HCID 178514763HCID 178514763, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 11.5 g of the hydrazide prepared in Example 1 in 100 ml of absolute ethanol was added a solution of 2.8 g of potassium hydroxide in 20 ml of water. After stirring several minutes, 4.8 g of carbon disulfide was added in one portion. The suspension was refluxed 4.5 hours then concentrated in vacuo. After water (about 100 ml) was added to the residue and the suspension stirred several minutes, the suspension was filtered and the filtrate was acidified with concentrated hydrochloric acid (red to litmus paper). The mixture was filtered and the residue was washed sequentially with 1×25 ml water, 1×10 ml 2-propanol and 1×10 ml ethyl ether. The suction-dried residue was recrystallized from methanol to give 3 g of the subject compound; m.p. 224°-227° C.

Workup

  1. temperatureThe suspension was refluxed 4.5 hours
  2. concentrationthen concentrated in vacuo
  3. additionAfter water (about 100 ml) was added to the residue
  4. stirringthe suspension stirred several minutes
  5. filtrationthe suspension was filtered
  6. filtrationThe mixture was filtered
  7. washthe residue was washed sequentially with 1×25 ml water, 1×10 ml 2-propanol and 1×10 ml ethyl ether
  8. customThe suction-dried residue was recrystallized from methanol

Sources & evidence

ORD record
ord-3d2b3310fed5434aaa19fa1a01b93994
Source dataset
uspto-grants-1987_10
Patent number
US04699649

Reaction notes

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