Sodium Chloride → HCID 23086900, compound

HRID 900835Notes

Reaction equation

HRID 900835 reaction equation
CS([C:5]1[N:9]=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[S:7][N:6]=1)(=O)=O.[CH2:17]([OH:22])[C:18]#[C:19][CH2:20][CH3:21].[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[Cl:16][C:12]1[CH:11]=[C:10]([C:8]2[S:7][N:6]=[C:5]([O:22][CH2:17][C:18]#[C:19][CH2:20][CH3:21])[N:9]=2)[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 804212-Pentyn-1-olHCID 23086908HCID 23086908, compound

Product 1

HCID 23086900HCID 23086900, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 2.5 ml of N,N-dimethylformamide, 350 mg of 3-methylsulfonyl-5-(3-chlorophenyl)-1,2,4-thiadiazole and 117 mg of 2-pentyne-1-ol were dissolved, to the resulting solution was added 56 mg of sodium hydride (60% oily) with ice-cooling, and the mixture was stirred for 30 minutes, and further stirred at room temperature for 1 hour. Then, the reaction mixture was poured into an aqueous saturated sodium chloride solution, and the mixture was extracted with t-butyl methyl ether. The residue obtained by concentration of the organic layer was subjected to silica gel column chromatography to obtain 290 mg of 5-(3-chlorophenyl)-3-(2-pentynyloxy)-1,2,4-thiadiazole (the compound (78) of the present invention).

Workup

  1. temperaturecooling
  2. stirringfurther stirred at room temperature for 1 hour
  3. extractionthe mixture was extracted with t-butyl methyl ether
  4. customThe residue obtained by concentration of the organic layer

Sources & evidence

ORD record
ord-6b1dc8549abb470a880fb9eca942676d
Source dataset
uspto-grants-2008_04
Patent number
US07361675B2

Reaction notes

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