Sodium hydride → HCID 19612613, compound

HRID 1600316Notes

Reaction equation

HRID 1600316 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 dropwise 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 (0.6 g, 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 waterand 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 dropwise 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-f7d3f5c5ec40433e981edff9acd048f3
Source dataset
uspto-grants-1998_04
Patent number
US05744489

Reaction notes

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