Ethylene Glycol → 5-(Ethylthio)pyridin-2-amine

HRID 2367857Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[CH2:9]([S-:11])[CH3:10].[Na+].C(O)CO>[Cu]>[CH2:9]([S:11][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=1)[CH3:10]

Participants

Conditions

Temperature: 150 °C

Procedure

2-Amino-5-iodo-pyridine (2.20 g; 10 mmol), sodium ethanethiolate 80% (1.7 g; 16 mmol) and copper powder (190 mg; 3.00 mmol) were loaded into a 100 mL round bottom flask under nitrogen. Ethylene glycol (40 mL; 0.25 mol) was added and the solution stirred at 150° C. for 26 h. The cooled solution was filtered and partitioned between ethyl acetate and water twice. The organic layer was dried over barium oxide, filtered and the solvent removed in vacuo to afford 1.2 g (yield 76%) of product as yellow oil. 1H-NMR (300 MHz; CDCl3), δ 8.06 (1H, d, 4JHH=2.1 Hz, Ar—H), 7.48 (1H, dd, 3JHH=8.7 Hz, 4JHH=2.4 Hz, Ar—H), 6.42 (1H, dd, 3JHH=8.7 Hz, 5JHH=0.6 Hz, Ar—H), 2.68 (2H, q, 3JHH=7.3 Hz, CH2), 1.15 (3H, t, 3JHH=7.2 Hz, CH3).

Workup

filtrationThe cooled solution was filtered
custompartitioned between ethyl acetate and water twice
dry with materialThe organic layer was dried over barium oxide
filtrationfiltered
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-8cdb4115178742fe9f58aaa47c4c0884
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703096B2

Reaction notes

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