Benzyl Alcohol → 5-Benzyloxy-3-benzylthio-1,2,4-thiadiazole

HRID 917332Notes

Reaction equation

HRID 917332 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[CH2:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[CH2:15]([O:22][C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 121513833-(Benzylsulfanyl)-5-chloro-1,2,4-thiadiazole

Product 1

HCID 121513845-Benzyloxy-3-benzylthio-1,2,4-thiadiazoleYield 46.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 3 ml of N,N-dimethylformamide were dissolved 243 mg of 5-chloro-3-benzylthio-1,2,4-thiadiazole and 108 mg of benzyl alcohol, 48 mg of sodium hydride (60% in oil) was added thereto under ice-cooling, and the reaction mixture was stirred for 1 hour under ice-cooling and for 17 hours at room temperature. The reaction mixture was added to saturated sodium chloride aqueous solution, and extracted with t-butyl methyl ether. The organic layer was concentrated, and the residue obtained was subjected to silica gel column chromatography to give 146 mg of 5-benzyloxy-3-benzylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (31)).

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. extractionextracted with t-butyl methyl ether
  4. concentrationThe organic layer was concentrated
  5. customthe residue obtained

Sources & evidence

ORD record
ord-2035caffa12a413a9a08f19e70da5278
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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