Carbon Disulfide → 2-[(5-Mercapto-1,3,4-thiadiazol-2-yl)methyl]benzenesulfonamide

HRID 231974Notes

Reaction equation

HRID 231974 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:12]([NH:14][NH2:15])=O)(=[O:4])=[O:3].[OH-].[K+].[C:18](=[S:20])=[S:19]>C(O)C.O>[SH:20][C:18]1[S:19][C:12]([CH2:11][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:2]([NH2:1])(=[O:4])=[O:3])=[N:14][N:15]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 159257202-(Aminosulfonyl)benzeneacetic acid, hydrazide

Product 1

HCID 1785147042-[(5-Mercapto-1,3,4-thiadiazol-2-yl)methyl]benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 22 g of the hydrazide prepared in Example 1 in 175 ml of absolute ethanol was added a solution of 5.4 g of potassium hydroxide in 40 ml of water. After stirring several minutes, 9.2 g of carbon disulfide was added dropwise. The suspension was refluxed 4 hours then concentrated in vacuo. After water (about 200 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 solid isolated was suction-dried to give 5 g of the crude subject compound; m.p. 173°-197° C.

Workup

  1. temperatureThe suspension was refluxed 4 hours
  2. concentrationthen concentrated in vacuo
  3. additionAfter water (about 200 ml) was added to the residue
  4. stirringthe suspension stirred several minutes
  5. filtrationthe suspension was filtered
  6. filtrationThe mixture was filtered
  7. customthe solid isolated
  8. customwas suction-dried
  9. customto give 5 g of the crude

Sources & evidence

ORD record
ord-00946351386c4392b76291c5c0cbf081
Source dataset
uspto-grants-1989_07
Patent number
US04851030

Reaction notes

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