Sodium hydride → HCID 19612613, compound

HRID 1291536Notes

Reaction equation

HRID 1291536 reaction equation
[H-].[Na+].[CH3:3][C:4]1[S:8][C:7]([CH2:9][CH2:10][CH2:11][OH:12])=[CH:6][CH:5]=1.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>C1COCC1>[CH3:3][C:4]1[S:8][C:7]([CH2:9][CH2:10][CH2:11][O:12][C:14]2[C:18]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[N:17][S:16][N:15]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 104881643-Chloro-4-(pyridin-3-yl)-1,2,5-thiadiazoleHCID 12862889HCID 12862889, compound

Product 1

HCID 19612613HCID 19612613, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (10.2 mmol) was added to a solution of 3-(5-methyl-2-thienyl)-1-propanol (4.0 g, 25.5 mmol) in THF (40 ml). The mixture was stirred for 1 h at room temperature, whereupon a solution of 3-(3-chloro-1,2,5-thiadiazol-4-yl)pyridine (1.0 g, 5.1 mmol) in THF (10 ml) was added drop-wise to the reaction mixture. After stirring overnight at room temperature, the reaction was quenched with water then extracted with diethyl ether. The organic phase was dried over NaCl/Na2 SO4 then evaporated to yield crude 3-(3-(5-methyl-2-thienyl)propoxy-1,2,5-thiadiazol-4-yl)pyridine. A solution of 3-(3-(5-methyl-2-thienyl)propoxy-1,2,5-thiadiazol-4-yl)pyridine (1.0 g, 3.2 mmol) and iodomethane (2.3 g, 16.0 mmol) in 60 ml of acetone was refluxed overnight. The solution was evaporated to yield 1.5 g of the quaternized product. Sodium borohydride (0.6g, 16.0 mmol) was carefully added to a solution of the quaternized product (1.5 g) in ethanol (30 ml). The reaction was evaporated and the resulting residue was taken up in water and extracted with methylene chloride (3×100 ml). The organic phase was dried over NaCl/Na2SO4 then evaporated. The residue was purified by radial chromatography eluting with 0.5% NH4OH/5.0% EtOH in CHCl3. The oxalate salt was made to yield 337 mg of the title compound. M.p. 134°-137° C.(Compound 129).

Workup

  1. additionwas added drop-wise to the reaction mixture
  2. customthe reaction was quenched with water
  3. extractionthen extracted with diethyl ether
  4. dry with materialThe organic phase was dried over NaCl/Na2 SO4
  5. customthen evaporated

Sources & evidence

ORD record
ord-3149a3db9f3d49889b2be9a995ced77a
Source dataset
uspto-grants-1998_05
Patent number
US05753683

Reaction notes

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