Thionyl Chloride → HCID 54474351, compound

HRID 1612948Notes

Reaction equation

HRID 1612948 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH2:10]O)[CH:5]=[N:6][CH:7]=1.S(Cl)([Cl:14])=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH2:10][Cl:14])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 24386Thionyl Chloride2×HCID 516892Sodium BicarbonateHCID 54176324HCID 54176324, compound

Product 1

HCID 54474351HCID 54474351, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(5-bromo-3-pyridinyl)prop-2-en-1-ol (0.85 gms, 3.97 mmol) is diluted with methylene chloride (20 mls). Thionyl chloride (0.27 mls, 97%, leq) is added at room temperature. After one hour a second equivalent of thionyl chloride is added. The reaction is neutralized with saturated aqueous NaHCO3 after an additional hour and extracted with methylene chloride. The organic layer is dried over Na2SO4 and evaporated to yield 0.70 gms of an oil (76%). 1H NMR (CDCl3, 300 MHz) δ8.90 (s, 1H), 8.70 (s, 1H), 8.40 (s, 1H), 6.70 (m, 2H), and 4.30 (d, J=3.8 Hz, 2H).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe organic layer is dried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-80e53a67765e4f8389401ce325afa588
Source dataset
uspto-grants-1993_03
Patent number
US05191084

Reaction notes

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