Sodium hydride → HCID 19612579, compound

HRID 581012Notes

Reaction equation

HRID 581012 reaction equation
[H-].[Na+].[F:3][C:4]([F:12])([F:11])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].Cl[C:14]1[C:18]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[N:17][S:16][N:15]=1>O1CCCC1>[F:3][C:4]([F:12])([F:11])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:14]1[C:18]([C:19]2[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=2)=[N:17][S:16][N:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 104881643-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazoleHCID 193493916,6,6-Trifluoro-1-hexanol

Product 1

HCID 19612579HCID 19612579, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of sodium hydride (12.8 mmol) and 6,6,6-trifluoro-1-hexanol (3.0 g, 19.2 mmol) in tetrahydrofuran (40 ml) was added 3-(3-chloro-1,2,5-thiadiazol-4-yl)pyridine (1.3 g, 6.4 mmol). The mixture was refluxed for 36 h. and evaporated. After evaporation the residue was dissolved in water then extracted with diethyl ether. The dried organic phases were evaporated and the residue purified by column chromatography (silica gel, eluent:ethyl acetate/hexanes) to yield 630 mg (31%) of the title compound.

Workup

  1. temperatureThe mixture was refluxed for 36 h.
  2. customevaporated
  3. customAfter evaporation the residue
  4. dissolutionwas dissolved in water
  5. extractionthen extracted with diethyl ether
  6. customThe dried organic phases were evaporated
  7. customthe residue purified by column chromatography (silica gel, eluent:ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bda21fb5d9f74dea914507028c395e58
Source dataset
uspto-grants-1999_07
Patent number
US05919805

Reaction notes

Loading…