Thionyl Chloride → HCID 86626539, compound

HRID 1698066Notes

Reaction equation

HRID 1698066 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 pyrrolidine (0.5 mL) in CH2Cl2 (1.5 mL). The reaction was stirred at r.t. for 1 h. Water was added and the reaction mixture was extracted, twice, with DCM, dried (MgSO4), filtered and the solvent was evaporated. The solid was dried (in vacuo over P2O5) to give the title compound (45 mg) as an off-white solid. 1H NMR δ 8.92 (d, 1H) 8.39 (dd, 1H) 8.35 (s, 1H) 8.07 (d, 1H) 7.67 (d, 1H) 7.04 (d, 1H) 3.97 (s, 3H) 3.51 (t, 2H) 3.45 (t, 2H) 1.78-1.95 (m, 4H); MS m/z (M+H) 340.

Workup

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

Sources & evidence

ORD record
ord-4937b3a377d84f309db27bf256521a7f
Source dataset
uspto-grants-2012_04
Patent number
US08163928B2

Reaction notes

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