Thionyl Chloride → HCID 57743012, compound

HRID 2043674Notes

Reaction equation

HRID 2043674 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([CH2:17]O)=[C:11]3[N:10]=[CH:9]2)=[CH:5][CH:4]=1.O=S(Cl)[Cl:23]>ClCCl>[Cl:23][CH2:17][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[N:8]([CH2:7][C:6]3[CH:19]=[CH:20][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:9]=[N:10][C:11]=12

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 57743081HCID 57743081, compound

Product 1

HCID 57743012HCID 57743012, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[3-(4-methoxybenzyl)-3H-imidazo[4,5-b]pyridin-7-yl]methanol x183 (0.5 g, 1.86 mmol) is dissolved in dichloromethane (20 ml). SOCl2 (2 ml) is added dropwise. The reaction mixture is refluxed for 1 h. The volatiles are distilled off in the vacuum of a rotary evaporator. Then 50 ml of chloroform is distilled off additionally from the residue. The residual chloroform solution is added dropwise at 0° C. to a vigorously stirred saturated aqueous solution of NaHCO3. The organic phase is separated, dried with anhydrous sodium sulfate, and evaporated. The residue is kept under 1 mmHg for 1.5 h at 40° C. to afford 7-(chloromethyl)-3-(4-methoxybenzyl)-3H-imidazo[4,5-b]pyridine x185 sufficiently pure for the next step.

Workup

  1. temperatureThe reaction mixture is refluxed for 1 h
  2. distillationThe volatiles are distilled off in the vacuum of a rotary evaporator
  3. distillationThen 50 ml of chloroform is distilled off additionally from the residue
  4. additionThe residual chloroform solution is added dropwise at 0° C. to a vigorously stirred saturated aqueous solution of NaHCO3
  5. customThe organic phase is separated
  6. dry with materialdried with anhydrous sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-75287195e4464fe1baae59186c1ef173
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

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