4-Hydroxymethylpyridine → 4-(Chloromethyl)pyridinium chloride

HRID 8410

Reaction equation

HRID 8410 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.S(Cl)([Cl:11])=O>C(#N)C>[ClH:11].[Cl:11][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 114724-HydroxymethylpyridineHCID 24386Thionyl Chloride

Product 1

HCID 745704-(Chloromethyl)pyridinium chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

4-Hydroxymethylpyridine (20) (54.4 g, 0.50 mol) was dissolved in acetonitrile 202 ml. The solution was added dropwise to a mixture of thionyl chloride (65.3 g, 0.55 mol) and acetonitrile (109 ml) under 50° C. The mixture was stirred at the same temperature for 1 hour, then cooled to room temperature to yield a slurry (quantitative) of the objective (21).

Sources & evidence

ORD record
ord-dee3bbe8fbf245858780f3dd89a7ddd2
Source dataset
uspto-grants-2006_08
Patent number
US07087764B2

Linked notes

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