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

HRID 33542Notes

Reaction equation

HRID 33542 reaction equation
S(Cl)([Cl:3])=O.CN(C)C=O.[Cl:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:18]=[C:19]([CH2:23]O)[CH:20]=[N:21][CH:22]=2)[CH:14]=[CH:15][CH:16]=1>ClCCl>[Cl:3][CH2:23][C:19]1[CH:20]=[N:21][CH:22]=[C:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([Cl:10])[CH:12]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 24729846(5-(3-Chlorophenyl)pyridin-3-yl)methanol

Product 1

HCID 691064073-(Chloromethyl)-5-(3-chlorophenyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

271 mg (0.165 ml, 2.28 mmol) thionyl chloride were added drop by drop at 0° C. to a solution of 0.2 ml N,N-dimethylformamide (DMF) and 250 mg (1.14 mmol) [5-(3-Chloro-phenyl)-pyridin-3-yl]-methanol in 20 ml dichloromethane and stirred for 3 h at 0° C. The mixture was poured on ice/sodium bicarbonate solution and the organic phase separated. The water phase was extracted with dichloromethane. The combined organic phases were washed with water, dried (sodium sulphate), evaporated and the obtained material (248 mg, 84%) used without further purification.

Workup

  1. additionThe mixture was poured on ice/sodium bicarbonate solution
  2. customthe organic phase separated
  3. extractionThe water phase was extracted with dichloromethane
  4. washThe combined organic phases were washed with water
  5. dry with materialdried (sodium sulphate)
  6. customevaporated
  7. customthe obtained material (248 mg, 84%) used without further purification

Sources & evidence

ORD record
ord-c4d58a1f9f3141559d0f09867fd52fcd
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

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