Thionyl Chloride → HCID 86626539, compound

HRID 1698065Notes

Reaction equation

HRID 1698065 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

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 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, 1H) 8.51-8.68 (m, 2H) 8.39 (dd, 1H) 8.09 (d, 1H) 7.98 (d, 1H) 7.04 (d, 1H) 3.97 (s, 3H) 2.83 (d, 3H); MS m/z (M+H) 300, (M−H) 298.

Workup

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

Sources & evidence

ORD record
ord-0c9d2e8e416640d6b872ef29082d1af2
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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