Dimethylformamide → 4-Chloro-2-chloromethyl-3-methoxypyridinium chloride

HRID 1819268Notes

Reaction equation

HRID 1819268 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH2:8]O)[C:3]=1[O:10][CH3:11].CN(C=O)C.S(Cl)([Cl:19])=O>C(Cl)Cl>[Cl-:1].[Cl:1][C:2]1[CH:7]=[CH:6][NH+:5]=[C:4]([CH2:8][Cl:19])[C:3]=1[O:10][CH3:11]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 11480736(4-Chloro-3-methoxypyridin-2-yl)methanol

Product 1

HCID 685400364-Chloro-2-chloromethyl-3-methoxypyridinium chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The resulting solution of 4-chloro-2-hydroxymethyl-3-methoxypyridine (−30% strength) was diluted with CH2Cl2 (48 L). DMF (65.5 g, 0.896 mol) was added in one portion and, then, thionyl chloride (11.1 kg, 93.2 mol) over 3-5 h at 15-30° C. After stirring for additional 1.5 h, about 45 L of solvents were distilled off. Toluene (20 L) was added and 20 L of solvents were again removed by distillation. Then, ethanol (1.5 L) was added to the resulting thick slurry. The solids were filtered off at 10-15° C., washed with toluene (17 L) and dried in vacuo at 30° C. to give 4-chloro-2-chloromethyl-3-methoxypyridinium chloride as an off-white solid (m. p. 132° C.); yield 15.0 kg (59%).

Workup

  1. distillationabout 45 L of solvents were distilled off
  2. additionToluene (20 L) was added
  3. custom20 L of solvents were again removed by distillation
  4. additionThen, ethanol (1.5 L) was added to the resulting thick slurry
  5. filtrationThe solids were filtered off at 10-15° C.
  6. washwashed with toluene (17 L)
  7. customdried in vacuo at 30° C.

Sources & evidence

ORD record
ord-3ee5d52d5e3f466d967babf30bd09692
Source dataset
uspto-grants-2009_10
Patent number
US07601737B2

Reaction notes

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