Thionyl Chloride → HCID 18621444, compound

HRID 1861781Notes

Reaction equation

HRID 1861781 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14]O)[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=S(Cl)[Cl:18]>>[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][Cl:18])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 18621466HCID 18621466, compound

Product 1

HCID 18621444HCID 18621444, compoundYield 100.7%

Procedure

A solution of 4-benzyl-2-(hydroxymethyl) pyridine (2.85 g, 14.6 mmol) in SOCl2 (7.50 mL, 102 mmol) was stirred at 25° C. for 30 min. and was concentrated under reduced pressure. The crude compound was diluted with EtOAc (100 mL), washed with NaHCO3 (2×100 mL), dried over Na2SO4 and was concentrated under reduced pressure to afford the title compound as a dark oil (3.2 g, 98%): 1H NMR (CDCl3) δ4.00 (s, 2H), 4.66 (s, 2H), 7.08 (d, J=5.1 Hz, 1H), 7.18 (d, J=7.2 Hz, 2H), 7.20-7.40 (m, 4H), 8.46 (d, J=5.1 Hz, 1H).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionThe crude compound was diluted with EtOAc (100 mL)
  3. washwashed with NaHCO3 (2×100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-813460f98d724a86a10739ef3cc5cb8b
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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