Dimethylformamide → 3-(Chloromethyl)-5-(4-chlorophenyl)pyridine

HRID 33534Notes

Reaction equation

HRID 33534 reaction equation
S(Cl)([Cl:3])=O.CN(C)C=O.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:18]=[C:19]([CH2:23]O)[CH:20]=[N:21][CH:22]=2)=[CH:13][CH:12]=1>ClCCl>[Cl:3][CH2:23][C:19]1[CH:20]=[N:21][CH:22]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 24729853(5-(4-Chlorophenyl)pyridin-3-yl)methanol

Product 1

HCID 691064233-(Chloromethyl)-5-(4-chlorophenyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

543 mg (0.333 ml, 4.56 mmol) thionyl chloride were added drop by drop at 0° C. to a solution of 0.2 ml N,N-dimethylformamide (DMF) and 500 mg (2.28 mmol) [5-(4-Chloro-phenyl)-pyridin-3-yl]-methanol in 30 ml dichloromethane and stirred for 2 h at 0° C. The mixture was poured on ice/sodium bicarbonate solution and the organic phase separated. The water phase is extracted with dichloromethane. The combined organic phases were washed with water, dried (sodium sulphate), evaporated and the obtained material (444 mg, 75%) used without further purification.

Workup

  1. additionThe mixture was poured on ice/sodium bicarbonate solution
  2. customthe organic phase separated
  3. extractionThe water phase is extracted with dichloromethane
  4. washThe combined organic phases were washed with water
  5. dry with materialdried (sodium sulphate)
  6. customevaporated
  7. customthe obtained material (444 mg, 75%) used without further purification

Sources & evidence

ORD record
ord-762e26e932fc4ce8b68c83898c1bd9b2
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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