Thionyl Chloride → 2-(2-Chloromethyl-benzo[b]thiophen-6-yloxy)-benzothiazole

HRID 1947484Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:12]=[CH:13][C:14]2[CH:18]=[C:17]([CH2:19]O)[S:16][C:15]=2[CH:21]=1.S(Cl)([Cl:24])=O>C(Cl)Cl>[Cl:24][CH2:19][C:17]1[S:16][C:15]2[CH:21]=[C:11]([O:10][C:2]3[S:1][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)[CH:12]=[CH:13][C:14]=2[CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution [6-(benzothiazol-2-yloxy)-benzo[b]thiophen-2-yl]-methanol (256 mg, 0.8 mmol) in DCM (8 mL) was added thionyl chloride (60 μL, 98 mg, 0.8 mmol) and the reaction mixture was stirred (0° C., 2 h). The reaction mixture was partitioned between EtOAc (20 mL) and saturated NaHCO3 (10 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×20 mL). The organic layer was dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using EtOAc:hexane (0-40%) to provide the title compound as yellow solid (0.17 g, 65%). MS (ESI): mass calcd. for C16H10ClNOS2, 331.0; m/z found, 332.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.84 (d, J=2.2, 1H), 7.78 (d, J=8.7, 1H), 7.74 (dd, J=8.1, 0.6, 1H), 7.68 (dd, J=8.0, 0.7, 1H), 7.43-7.26 (m, 4H), 4.86 (s, 2H).

Workup

customThe reaction mixture was partitioned between EtOAc (20 mL) and saturated NaHCO3 (10 mL)
customThe organic layer was separated
extractionthe aqueous layer was extracted with EtOAc (2×20 mL)
customThe organic layer was dried
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting residue was purified by silica gel flash chromatography

Sources & evidence

ORD record: ord-a06ede2b7b17407daf704110c750c31d
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399465B2

Reaction notes

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