Benzyl Alcohol → HCID 18619208, compound

HRID 1862340Notes

Reaction equation

HRID 1862340 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H].[Cl:13][C:14]1[C:18](Cl)=[N:17][S:16][N:15]=1>O1CCCC1>[CH2:3]([O:10][C:18]1[C:14]([Cl:13])=[N:15][S:16][N:17]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 798043,4-Dichloro-1,2,5-thiadiazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 18619208HCID 18619208, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-50 °C

Procedure

To a mixture of 24 g of sodium hydride and 500 ml of tetrahydrofuran, 65 g of benzyl alcohol was added dropwise at room temperature. The mixture was stirred until the evolution of hydrogen stopped, cooled to −50° C., then, 100 g of 3,4-dichloro-1,2,5-thiadiazole was added to the mixture. The mixture was stirred over night at room temperature, and for 3 hours at reflux temperature. The mixture was concentrated, then poured into dilute hydrochloric acid, extracted with t-butyl methyl ether. The organic layer was washed with water, then, saturated saline, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 33 g of 4-benzyloxy-3-chloro-1,2,5-thiadiazole (purity: 72%).

Workup

  1. additionwas added dropwise at room temperature
  2. temperaturefor 3 hours at reflux temperature
  3. concentrationThe mixture was concentrated
  4. additionpoured into dilute hydrochloric acid
  5. extractionextracted with t-butyl methyl ether
  6. washThe organic layer was washed with water
  7. dry with materialsaturated saline, dried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4287e32e307945d8b9fff8f3bcdb0da7
Source dataset
uspto-grants-2003_03
Patent number
US06537948B1

Reaction notes

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