Thionyl Chloride → 3,3'-(Chloromethylene)dipyridine

HRID 2278170Notes

Reaction equation

HRID 2278170 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)O)[CH:2]=1.S(Cl)([Cl:17])=O>C(Cl)Cl>[Cl:17][CH:7]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 11309949Dipyridin-3-ylmethanol

Product 1

HCID 574257823,3'-(Chloromethylene)dipyridineYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round bottom flask was charged with di(pyridin-3-yl)methanol (600 mg, 3.22 mmol) and CH2Cl2 (50 mL). Thionyl chloride (353 μl, 4.83 mmol) was added and the reaction was stirred for 18 h at room temperature. The solution was concentrated under reduced pressure. The residue was chromatographed on a silica gel column (100% CH2Cl2 to 5% 2M NH3 in MeOH) and yielded 3,3′-(chloromethylene)dipyridine (415 mg, 64%). 1H NMR 400 MHz (CDCl3) δ 8.66 (d, J=2.4 Hz, 2H), 8.59 (dd, J=4.7, 1.6 Hz, 2H), 7.76 (m, 2H), 7.34 (m, 2H), 6.17 (s, 1H).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customThe residue was chromatographed on a silica gel column (100% CH2Cl2 to 5% 2M NH3 in MeOH)

Sources & evidence

ORD record
ord-a9837f52693a4ef89c4ae1b8bbfce34b
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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