Thionyl Chloride → HCID 57743065, compound

HRID 1924318Notes

Reaction equation

HRID 1924318 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]2[C:12]3=[N:13][C:14]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:16]([CH2:17]O)=[C:11]3[N:10]=[CH:9]2)=[CH:5][CH:4]=1.O=S(Cl)[Cl:27]>ClCCl>[Cl:27][CH2:17][C:16]1[CH:15]=[C:14]([C:19]([F:22])([F:21])[F:20])[N:13]=[C:12]2[N:8]([CH2:7][C:6]3[CH:23]=[CH:24][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 57743023HCID 57743023, compound

Product 1

HCID 57743065HCID 57743065, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[3-(4-methoxybenzyl)-5-(trifluoromethyl)-3H-imidazo[4,5-b]pyridin-7-yl]methanol x199 (0.55 g, 1.63 mmol) is dissolved in dichloromethane (20 ml). SOCl2 (2 ml) is added dropwise. The reaction mixture is refluxed for 1 h. The volatiles are rotary-evaporated. Then 50 ml of chloroform is additionally distilled off from the residue. The resulting chloroform solution is added dropwise at 0° C. under vigorous stirring to saturated aqueous NaHCO3. The organic phase is separated, dried with anhydrous sodium sulfate, evaporated, and dried under 1 mmHg for 1.5 h at 40° C. 7-(chloromethyl)-3-(4-methoxybenzyl)-5-(trifluoromethyl)-3H-imidazo[4,5-b]pyridine x202 (0.55 g, 95%) sufficiently pure for the next step is obtained.

Workup

  1. temperatureThe reaction mixture is refluxed for 1 h
  2. customThe volatiles are rotary-evaporated
  3. distillationThen 50 ml of chloroform is additionally distilled off from the residue
  4. additionThe resulting chloroform solution is added dropwise at 0° C.
  5. customThe organic phase is separated
  6. dry with materialdried with anhydrous sodium sulfate
  7. customevaporated
  8. customdried under 1 mmHg for 1.5 h at 40° C

Sources & evidence

ORD record
ord-0b7d51985c984bbaadec05d9085da27b
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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