Thionyl Chloride → 189449-56-7

HRID 1108434Notes

Reaction equation

HRID 1108434 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[Cl:13]>CN(C=O)C>[ClH:3].[Cl:3][CH2:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[Cl:13]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 435084(4-chloropyridin-3-yl)methanol

Product 1

HCID 18703042189449-56-7Yield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Thionyl chloride (0.714 mL, 9.78 mmol) was added at room temperature to dry DMF (7 mL). After 30 min the above solution was cannulated into the solution of 3-hydroxymethyl-4-chloropyridine (700 mg, 4.89 mmol) in DMF (3 mL). After 45 min, the product was precipitated by addition of dry ether (100 ml), washed with ether, and dried in vacuum to yield 813 mg (84%) of the title compound. 1H NMR (CD3OD) δ 5.00 (s, 2H), 8.31 (d, 1H, J=5), 8.99 (d, 1H, J=5), 9.18 (s, 1H).

Workup

  1. customthe product was precipitated by addition of dry ether (100 ml)
  2. washwashed with ether
  3. customdried in vacuum

Sources & evidence

ORD record
ord-fe75b454e0054238a342db8b05ff6fd6
Source dataset
uspto-grants-2000_05
Patent number
US06066630

Reaction notes

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