Thionyl Chloride → 189449-56-7

HRID 342939Notes

Reaction equation

HRID 342939 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=S), 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-4731beb0a8ea429b98408874d461c7ad
Source dataset
uspto-grants-1999_01
Patent number
US05859256

Reaction notes

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