Sodium Chloride → 5-(6-Quinolyl)-1,3,4-oxadiazole-2-thiol

HRID 452615Notes

Reaction equation

HRID 452615 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([NH:13][NH2:14])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:15](=S)=[S:16].C(N(CC)CC)C.[Cl-].[NH4+].[Cl-].[Na+]>C(O)C.O>[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[O:12][C:15]([SH:16])=[N:14][N:13]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 456707Quinoline-6-carbohydrazide

Product 1

HCID 1785279365-(6-Quinolyl)-1,3,4-oxadiazole-2-thiolYield 51%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of quinoline-6-carbohydrazide (2.00 g, 10.7 mmol), carbon disulfide (1.61 mL, 26.8 mmol) and triethylamine (1.78 mL, 12.8 mmol) in ethanol (40 mL) was heated under reflux for 4 hr. After cooling, the reaction mixture was poured into water, a saturated aqueous ammonium chloride solution (100 mL) was added, and the mixture was saturated with sodium chloride. The precipitate was collected by filtration and recrystallized from methanol to give the title compound (1.24 g, yield 51%) as pale-yellow crystals.

Workup

  1. temperatureunder reflux for 4 hr
  2. temperatureAfter cooling
  3. filtrationThe precipitate was collected by filtration
  4. customrecrystallized from methanol

Sources & evidence

ORD record
ord-1dea1cc0d25148fe96e364baebcaeaab
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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