Sodium Chloride → HCID 11680117, compound

HRID 900829Notes

Reaction equation

HRID 900829 reaction equation
CS([C:4]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[S:6][N:5]=1)=O.CS(C1N=C(C2C=CC=CC=2)SN=1)(=O)=O.[CH2:30]([OH:33])[C:31]#[CH:32].[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[C:9]1([C:7]2[S:6][N:5]=[C:4]([O:33][CH2:30][C:31]#[CH:32])[N:8]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 23086893HCID 23086893, compoundHCID 23086911HCID 23086911, compound

Product 1

HCID 11680117HCID 11680117, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3 ml of N,N-dimethylformamide were added 160 mg of a mixture of 3-methylsulfinyl-5-phenyl-1,2,4-thiadiazole and 3-methylsulfonyl-5-phenyl-1,2,4-thiadiazole (integration ratio of 1H-NMR sulfonyl form:sulfinyl form=4:1) and 60 mg of propargyl alcohol, and to the resulting mixture was added 43 mg of sodium hydride (60% oily) with ice-cooling. The mixture was stirred for 20 minutes with ice-cooling, and allowed to stand at room temperature for 18 hours. Then, 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 resulting residue was subjected to silica gel column chromatography to obtain 100 mg of 5-phenyl-3-propargyloxy-1,2,4-thiadiazole (the compound (1) of the present invention).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. waitto stand at room temperature for 18 hours
  4. extractionthe mixture was extracted with t-butyl methyl ether
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-18ce1775fed8444791bfd6478ebedfe8
Source dataset
uspto-grants-2008_04
Patent number
US07361675B2

Reaction notes

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