Benzyl Alcohol → HCID 58962893, compound

HRID 917341Notes

Reaction equation

HRID 917341 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.[CH2:17]([OH:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[CH2:17]([O:24][C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 23032434HCID 23032434, compound

Product 1

HCID 58962893HCID 58962893, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 3 g of N,N-dimethylformamide were dissolved 350 mg of 5-chloro-3-benzyloxymethylthio-1,2,4-thiadiazole and 153 mg of benzyl alcohol, 68 mg of sodium hydride (60% in oil) was added thereto under ice-cooling, and the reaction mixture was stirred for 30 minutes. After stirring for 2 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 260 mg of 5-bezyloxy-3-benzyloxymethythio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (43)).

Workup

  1. additionwas added
  2. temperatureunder ice-cooling
  3. stirringAfter stirring for 2 hours at room temperature
  4. extractionextracted with t-butyl methyl ether
  5. concentrationThe organic layer was concentrated
  6. customthe residue obtained

Sources & evidence

ORD record
ord-b8ee7cd9247148a98a88f427fb107c6a
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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