Carbon Disulfide → 5-(4-Methoxybenzyl)-1,3,4-oxadiazole-2-thiol

HRID 618200Notes

Reaction equation

HRID 618200 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([NH:14][NH2:15])=[O:13])=[CH:7][CH:6]=1.[C:16](=S)=[S:17]>O.C(O)C>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]2[O:13][C:16](=[S:17])[NH:15][N:14]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 5784632-(4-Methoxyphenyl)acetohydrazide

Product 1

HCID 11331125-(4-Methoxybenzyl)-1,3,4-oxadiazole-2-thiol

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of potassium hydroxide (0.7 g) in water (2 cm3) was added to a stirred solution of (4-methoxyphenyl)acetic acid hydrazide (1.99 g) in ethanol (30 cm3). carbon disulfide (0.7 cm3) was added and the reaction was heated to reflux for 6 hours and then left to cool. The reaction mixture was evaporated to dryness under reduced pressure and the solid residue dissolved in water. The pH was adjusted to 1 with concentrated hydrochloric acid, resulting in formation of a white precipitate. The precipitate was isolated by filtration, washed with water and ether and air dried to give 5-(4-methoxybenzyl)-1,3,4-oxadiazole-2(3H)-thione (1.96 g). M+ =222; 1H NMR: δ 3.80(3H,s); 3.95(2H,s); 6.90(2H,d); 7.20(2H,d); (solid).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 6 hours
  3. waitleft
  4. temperatureto cool
  5. customThe reaction mixture was evaporated to dryness under reduced pressure
  6. dissolutionthe solid residue dissolved in water
  7. customresulting in formation of a white precipitate
  8. customThe precipitate was isolated by filtration
  9. washwashed with water and ether and air
  10. customdried

Sources & evidence

ORD record
ord-0092121526964ceca9d6035a9f4a2cad
Source dataset
uspto-grants-1999_09
Patent number
US05952359

Reaction notes

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