Carbon Disulfide → HCID 178527966, compound

HRID 1710020Notes

Reaction equation

HRID 1710020 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][NH2:12])=[O:10])=[CH:4][CH:3]=1.[C:13](=S)=[S:14].[OH-].[K+]>O.C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[O:10][C:13]([SH:14])=[N:12][N:11]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 4567342-(4-Chlorophenyl)acetohydrazide

Product 1

HCID 178527966HCID 178527966, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A stirred solution of 7.0 grams (0.038 mole) of 4-chlorophenylacetic acid hydrazide, 3.0 grams (0.039 mole) of carbon disulfide and 2.8 grams (0.050 mole) of potassium hydroxide in 10 ml of water and 200 ml of ethanol was heated under reflux for four hours. The ethanol was removed under reduced pressure. The concentrate was taken up in water and the mixture washed with diethyl ether. The aqueous layer was acidified with aqueous 5% hydrochloric acid and then was extracted with diethyl ether. The extract was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to yield 3.9 grams of 2-(4-chlorophenylmethyl)-5-mercapto-1,3,4-oxadiazole; m.p. 115° C. The nmr spectrum was consistent with the proposed structure.

Workup

  1. temperatureunder reflux for four hours
  2. customThe ethanol was removed under reduced pressure
  3. washthe mixture washed with diethyl ether
  4. extractionwas extracted with diethyl ether
  5. dry with materialThe extract was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c29c8c2882ca4f849186c24e39a7bac7
Source dataset
uspto-grants-1990_08
Patent number
US04952580

Reaction notes

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