Thionyl Chloride → 2-[4-(Chloromethyl)phenoxy][1,3]thiazolo[4,5-b]pyridine

HRID 1807450Notes

Reaction equation

HRID 1807450 reaction equation
[S:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]1[O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17]O)=[CH:13][CH:12]=1.O=S(Cl)[Cl:21]>C(Cl)Cl>[Cl:21][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([O:10][C:2]2[S:1][C:9]3[C:4]([N:3]=2)=[N:5][CH:6]=[CH:7][CH:8]=3)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 24386Thionyl Chloride2×HCID 57448385[4-([1,3]Thiazolo[4,5-b]pyridin-2-yloxy)phenyl]methanol

Product 1

HCID 574484032-[4-(Chloromethyl)phenoxy][1,3]thiazolo[4,5-b]pyridineYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [4-([1,3]thiazolo[4,5-b]pyridin-2-yloxy)phenyl]methanol (1.0 equiv.) in CH2Cl2 (0.3 M), SOCl2 (1.2 equiv.) was slowly added over 1 h at rt. In some embodiments, an excess of thionyl chloride was used, which was distilled off prior to the subsequent reaction step. After stirring at rt for another 30 min, the precipitated solid was collected by filtration and washed with CH2Cl2 to afford the title compound (100%), which was used without further purification. MS (ESI): mass calcd. for C13H9ClN2OS, 276.0; m/z found, 277.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6): 8.55 (dd, J=4.9, 1.7, 1H), 8.47 (dd, J=8.0, 1.7, 1H), 7.62 (dt, J=8.7, 2.1, 2H), 7.52 (dt, J=8.7, 2.1, 2H), 7.39 (dd, J=8.0, 4.9, 1H), 6.42 (br s, 1H), 4.84 (s, 2H).

Workup

  1. distillationwhich was distilled off
  2. customto the subsequent reaction step
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-eb077557c24c4f769eab961d05258b9f
Source dataset
uspto-grants-2013_01
Patent number
US08357684B2

Reaction notes

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