Water → HCID 58792115, compound

HRID 2222132Notes

Reaction equation

HRID 2222132 reaction equation
CS([C:5]1[N:9]=[C:8]([N:10]2[CH2:15][CH:14]([CH3:16])[CH2:13][CH:12]([CH3:17])[CH2:11]2)[S:7][N:6]=1)(=O)=O.[CH2:18]([OH:21])[C:19]#[CH:20].[H-].[Na+].O>CN(C)C=O>[CH2:18]([O:21][C:5]1[N:9]=[C:8]([N:10]2[CH2:15][CH:14]([CH3:16])[CH2:13][CH:12]([CH3:17])[CH2:11]2)[S:7][N:6]=1)[C:19]#[CH:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 69220520HCID 69220520, compound

Product 1

HCID 58792115HCID 58792115, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 3 ml of N,N-dimethylformamide were dissolved 373 mg of 3-methylsulfonyl-5-(3,5-dimethylpiperidino)-1,2,4-thiadiazole and 84 mg of 2-propyn-1-ol, and 71 mg of sodium hydride (oil suspension; content: 60 weight %) was added under ice-cooling. The mixture was stirred for 15 minutes and at room temperature for 1.5 hour. The reaction mixture was poured to water, and extracted with tert-butyl methyl ether. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 326 mg of 3-(2-propynyloxy)-5-(3,5-dimethylpiperidino)-1,2,4-thiadiazole (hereinafter, referred to as the present compound (20)).

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. extractionextracted with tert-butyl methyl ether
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d43819076bc34e2faa535b213aa3afa1
Source dataset
uspto-grants-2008_05
Patent number
US07371746B2

Reaction notes

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