Benzyl Alcohol → HCID 12151386, compound

HRID 917333Notes

Reaction equation

HRID 917333 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]([Cl:15])=[CH:11][CH:10]=2)[N:3]=1.[CH2:16]([OH:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Na+].[Cl-].[Na+]>CN(C)C=O>[CH2:16]([O:23][C:2]1[S:6][N:5]=[C:4]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)[N:3]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 12151385HCID 12151385, compound

Product 1

HCID 12151386HCID 12151386, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into 3 ml of N,N-dimethylformamide were dissolved 416 mg of 5-chloro-3-(4-chlorobenzylthio)-1,2,4-thiadiazole and 162 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 15 minutes under ice-cooling and for 1 hour 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 400 mg of 5-benzyloxy-3-(4-chlorobenzyl)thio-1,2,4-thiadiazole (hereinafter, referred to as the present compound (32)).

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-b31dbf901ecc4e3fa3b9e1ee47378e14
Source dataset
uspto-grants-2007_09
Patent number
US07273879B2

Reaction notes

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