Sodium hydride → HCID 69026216, compound

HRID 1594410Notes

Reaction equation

HRID 1594410 reaction equation
CS([C:5]1[N:9]=[C:8]([CH:10]2[CH2:15][CH:14]3[CH2:16][CH:11]2[CH2:12][CH2:13]3)[S:7][N:6]=1)(=O)=O.[CH2:17]([OH:22])[C:18]#[C:19][CH2:20]C.[H-].[Na+]>CN(C)C=O.[Cl-].[Na+].O>[CH:11]12[CH2:16][CH:14]([CH2:13][CH2:12]1)[CH2:15][CH:10]2[C:8]1[S:7][N:6]=[C:5]([O:22][CH2:17][C:18]#[C:19][CH3:20])[N:9]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 804212-Pentyn-1-olHCID 69025604HCID 69025604, compound

Product 1

HCID 69026216HCID 69026216, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

300 mg of 3-methylsulfonyl-5-(2-norbornyl)-1,2,4-thiadiazole and 107 mg of 2-pentyn-1-ol were dissolved in 2.5 g of N,N-dimethylformamide, 60 mg of sodium hydride (60% in oil) was added thereto under ice-cooling, and the reaction mixture was stirred for 30 minutes under ice-cooling and for 1 hour under room temperature. Then, the reaction mixture was added to saturated brine, and extracted with t-butyl methyl ether. The organic layer was concentrated under reduced pressure, and the residue obtained was subjected to silica gel column chromatography to give 5-(2-norbornyl)-3-(2-butynyloxy)-1,2,4-thiadiazole. 150 mg of the exo-isomer having low polarity (hereinafter referred to as the present invention compound (9-1)) and 50 mg of the endo-isomer having high polarity (hereinafter referred to as the present invention compound (9-2)) were obtained by using hexane-ethyl acetate system as a carrier solvent.

Workup

  1. temperatureunder ice-cooling
  2. extractionextracted with t-butyl methyl ether
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe residue obtained

Sources & evidence

ORD record
ord-ec88bb3467c040f7a877f91befef6bd0
Source dataset
uspto-grants-2007_11
Patent number
US07301032B2

Reaction notes

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