Dimethylformamide → 2-Chloromethyl-6-(3-chloro-phenyl)-pyridine

HRID 33538Notes

Reaction equation

HRID 33538 reaction equation
S(Cl)([Cl:3])=O.CN(C)C=O.[Cl:10][C:11]1[CH:12]=[C:13]([C:17]2[N:22]=[C:21]([CH2:23]O)[CH:20]=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1>ClCCl>[Cl:3][CH2:23][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([Cl:10])[CH:12]=2)[N:22]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 24730102[6-(3-Chloro-phenyl)-pyridin-2-yl]-methanol

Product 1

HCID 691064912-Chloromethyl-6-(3-chloro-phenyl)-pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

433 mg (0.264 ml, 3.64 mmol) thionyl chloride were added drop by drop at 0° C. to a solution of 0.2 ml N,N-dimethylformamide (DMF) and 400 mg (1.82 mmol) [6-(3-Chloro-phenyl)-pyridin-2-yl]-methanol in 25 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 is extracted with dichloromethane. The combined organic phases were washed with water, dried (sodium sulphate), evaporated and the obtained material (409 mg, 94%) 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 (409 mg, 94%) used without further purification

Sources & evidence

ORD record
ord-9ea2ea3cc39f474c846b72526298fff8
Source dataset
uspto-grants-2008_09
Patent number
US07429605B2

Reaction notes

Loading…