Benzyl Alcohol → HCID 12151382, compound

HRID 917331Notes

Reaction equation

HRID 917331 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][CH:9]=[CH2:10])[N:3]=1.[CH2:11]([OH:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[CH2:11]([O:18][C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][CH:9]=[CH2:10])[N:3]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 12151381HCID 12151381, compound

Product 1

HCID 12151382HCID 12151382, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 4 ml of N,N-dimethylformamide were dissolved 193 mg of 5-chloro-3-allylthio-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. 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 240 mg of 5-benzyloxy-3-allylthio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (30)).

Workup

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

Sources & evidence

ORD record
ord-7db2ad919ba144698bb90ea40f6a652a
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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