Benzyl Alcohol → HCID 12151388, compound

HRID 917334Notes

Reaction equation

HRID 917334 reaction equation
Cl[C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=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][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=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 12151387HCID 12151387, compound

Product 1

HCID 12151388HCID 12151388, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 2 ml of N,N-dimethylformamide were dissolved 200 mg of 5-chloro-3-(4-methoxybenzyl)thio-1,2,4-thiadiazole and 87 mg of benzyl alcohol, 35 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 4 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 165 mg of 5-benzyloxy-3-(4-methoxybenzyl)thio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (33)).

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-9a5e5ae9c8f84975908dba83c465893b
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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