Thionyl Chloride → HCID 59577637, compound

HRID 1947494Notes

Reaction equation

HRID 1947494 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:21]=[CH:20][C:14]2[C:15]([CH2:18]O)=[CH:16][O:17][C:13]=2[CH:12]=1.O=S(Cl)[Cl:24]>C(Cl)Cl>[Cl:24][CH2:18][C:15]1[C:14]2[CH:20]=[CH:21][C:11]([O:10][C:2]3[S:1][C:9]4[C:4]([N:3]=3)=[N:5][CH:6]=[CH:7][CH:8]=4)=[CH:12][C:13]=2[O:17][CH:16]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68771531HCID 68771531, compound

Product 1

HCID 59577637HCID 59577637, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [6-(thiazolo[4,5-b]pyridin-2-yloxy)-benzofuran-3-yl]-methanol (1.0 g, 3.4 mmol) in DCM (34 mL) was added SOCl2 (0.49 mL, 0.83 g, 7.0 mmol) and the reaction mixture was stirred (rt, 2 h). The reaction mixture was filtered to afford the hydrochloride salt of the title compound as a yellow solid (1.0 g, 84%). MS (ESI): mass calcd. for C15H9ClN2O2S, 316.01; m/z found, 317.0 [M+H]+. 1H NMR (400 MHz, CD3OD): 8.93 (dd, J=8.1, 1.4, 1H), 8.69 (dd, J=5.9, 1.4, 1H), 8.02 (s, 1H), 7.90 (d, J=8.5, 1H), 7.81-7.75 (m, 2H), 7.45 (dd, J=8.5, 2.2, 1H), 4.90 (s, 2H).

Workup

  1. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-4c050a59be214a97b7d38a26f08d63ab
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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