Thionyl Chloride → HCID 86626539, compound

HRID 1851745Notes

Reaction equation

HRID 1851745 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 (30 mg, 0.10 mmol) was mixed with thionyl chloride (0.8 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 ammonium hydroxide (cone., 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 (23 mg) as a yellow solid. 1H NMR δ 8.93 (d, 1 H) 8.64 (s, 1 H) 8.39 (dd, 1 H) 7.95-8.19 (m, 3 H) 7.50 (s, 1 H) 7.04 (d, 1 H) 3.97 (s, 3 H); MS m/z (M+H) 286, (M−H) 284.

Workup

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

Sources & evidence

ORD record
ord-a10211c1789a4655b31e8815985b5959
Source dataset
uspto-grants-2015_02
Patent number
US08957215B2

Reaction notes

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