Sodium Chloride → HCID 23086894, compound

HRID 900832Notes

Reaction equation

HRID 900832 reaction equation
CS([C:4]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])[S:6][N:5]=1)=O.CS(C1N=C(C2C=CC=CC=2F)SN=1)(=O)=O.[CH2:32]([OH:36])[C:33]#[C:34][CH3:35].[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:7]1[S:6][N:5]=[C:4]([O:36][CH2:32][C:33]#[C:34][CH3:35])[N:8]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 129912-Butyn-1-olHCID 24758Sodium hydrideHCID 23086892HCID 23086892, compoundHCID 23086896HCID 23086896, compound

Product 1

HCID 23086894HCID 23086894, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2 ml of N,N-dimethylformamide were added 295 mg of a mixture of 3-methylsulfinyl-5-(2-fluorophenyl)-1,2,4-thiadiazole and 3-methylsulfonyl-5-(2-fluorophenyl)-1,2,4-thiadiazole (integration ratio of 1H-NMR sulfonyl form:sulfinyl form=4:1) and 85 mg of 2-butyne-1-ol, to the resulting mixture was added 55 mg of sodium hydride (60% oily) with ice-cooling, and the mixture was stirred for 10 minutes, and further stirred at room temperature for 3 hours. The reaction mixture was poured into an aqueous saturated sodium chloride solution, and the mixture was extracted with t-butyl methyl ether. The organic layer was concentrated, and the residue was subjected to silica gel column chromatography to obtain 227 mg of 5-(2-fluorophenyl)-3-(2-butynyloxy)-1,2,4-thiadiazole (the compound (5) of the present invention).

Workup

  1. temperaturecooling
  2. stirringfurther stirred at room temperature for 3 hours
  3. extractionthe mixture was extracted with t-butyl methyl ether
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-dd9a979693af4cfe97479af11accd403
Source dataset
uspto-grants-2008_04
Patent number
US07361675B2

Reaction notes

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