2-Butyn-1-ol → 5-(Cyclohexyl)methyl-3-(2-butynyloxy)-1,2,4-thiadiazole

HRID 1594409Notes

Reaction equation

HRID 1594409 reaction equation
CS([C:5]1[N:9]=[C:8]([CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[S:7][N:6]=1)(=O)=O.[CH2:17]([OH:21])[C:18]#[C:19][CH3:20].[H-].[Na+]>CN(C)C=O.[Cl-].[Na+].O>[CH:11]1([CH2:10][C:8]2[S:7][N:6]=[C:5]([O:21][CH2:17][C:18]#[C:19][CH3:20])[N:9]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 690245423-Methylsulfonyl-5-(cyclohexyl)methyl-1,2,4-thiadiazole

Product 1

HCID 586104135-(Cyclohexyl)methyl-3-(2-butynyloxy)-1,2,4-thiadiazoleYield 77%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

300 mg of 3-methylsulfonyl-5-(cyclohexyl)methyl-1,2,4-thiadiazole and 89 mg of 2-butyn-1-ol were dissolved in 2.5 g of N,N-dimethylformamide, 55 mg of sodium hydride (60% in oil) was added thereto, and the reaction mixture was stirred for 30 minutes under ice-cooling. 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 222 mg of 5-(cyclohexyl)methyl-3-(2-butynyloxy)-1,2,4-thiadiazole (hereinafter referred to as the present invention compound (5)).

Workup

  1. temperaturecooling
  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-7edab9c10b3d4a2e95a0d747cd1917bb
Source dataset
uspto-grants-2007_11
Patent number
US07301032B2

Reaction notes

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