Thionyl Chloride → HCID 86626539, compound

HRID 1851746Notes

Reaction equation

[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([C:18]([OH:20])=O)[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:23])=O>>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([C:18]([Cl:23])=[O:20])[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][CH:4]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 24803401HCID 24803401, compound

Product 1

HCID 86626539HCID 86626539, compound

Procedure

2-(6-Methoxypyridin-3-yl)-1,3-benzothiazole-6-carboxylic acid (40 mg, 0.14 mmol) was mixed with thionyl chloride (1 mL) and stirred at r.t. for 3 h, then heated to 50° C. for 1 h. The solvent was evaporated in vacuo to give the intermediate 2-(6-methoxypyridin-3-yl)-1,3-benzothiazole-6-carbonyl chloride as a crude product. This acid chloride was dissolved in DCM (3 mL) and added to methylamine (40% in methanol, 2 mL). The reaction was stirred at r.t. without stopper overnight. The formed solid was collected by filtration, washed with water and dried (in vacuo over P2O5) to give the title compound (35 mg) as a light yellow solid. 1H NMR δ 8.92 (d, 1 H) 8.51-8.68 (m, 2 H) 8.39 (dd, 1 H) 8.09 (d, 1H) 7.98 (d, 1 H) 7.04 (d, 1 H) 3.97 (s, 3 H) 2.83 (d, 3 H); MS m/z (M+H) 300, (M−H) 298.

Workup

temperatureheated to 50° C. for 1 h
customThe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-cb5d7693cbd74b5f9dc4f8b16fc97a42
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957215B2

Reaction notes

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