Benzyl Chloride → HCID 178420436, compound

HRID 1278160Notes

Reaction equation

HRID 1278160 reaction equation
[SH:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.C[O-].[Na+].[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CO>[CH2:10]([S:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 10942334Sodium MethoxideHCID 178527894HCID 178527894, compound

Product 1

HCID 178420436HCID 178420436, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 30 g (0.29 m) 3-mercapto-1,2,4-triazole in 300 ml of dry methanol containing 16.0 g (0.29 m) sodium methoxide is stirred under dry conditions, cooled to 5° C. and benzylchloride 41.3 g (0.32 m) is added dropwise. Stir the mixture at room temperature overnight, reflux 2 hours, cool and evaporate to dryness. The residue is stirred in water and the product is extracted with ethyl acetate. Dry the ethyl acetate layer and evaporate to dryness to give white product. Recrystallize from toluene-hexane, white crystals, 41.4 g (73%), m.p. 79°-80° C.

Workup

  1. temperaturereflux 2 hours
  2. temperaturecool
  3. customevaporate to dryness
  4. stirringThe residue is stirred in water
  5. extractionthe product is extracted with ethyl acetate
  6. dry with materialDry the ethyl acetate layer
  7. customevaporate to dryness
  8. customto give white product
  9. customRecrystallize from toluene-hexane, white crystals, 41.4 g (73%), m.p. 79°-80° C.

Sources & evidence

ORD record
ord-bd9e18caa93c448c95c2396de5a49552
Source dataset
uspto-grants-1981_07
Patent number
US04280831

Reaction notes

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