Ethanol → 6-ethoxy-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridin-2-amine
Reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH2:11][C:12]2[S:16][C:15]([Cl:17])=[N:14][CH:13]=2)[CH2:9][CH3:10])[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][CH:3]=1.[Na].[CH2:22]([OH:24])[CH3:23]>>[CH2:22]([O:24][C:2]1[N:7]=[C:6]([N:8]([CH2:11][C:12]2[S:16][C:15]([Cl:17])=[N:14][CH:13]=2)[CH2:9][CH3:10])[C:5]([N+:18]([O-:20])=[O:19])=[CH:4][CH:3]=1)[CH3:23]Participants
Procedure
2.30 g of 6-chloro-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridine-2-amine (prepared in example 1) in ethanol (5 mL) was added dropwise to 0.16 g of sodium metal in 10 mL of anhydrous ethanol, the reaction mixture stirred at the room temperature for 2 to 6 hours, then treated according to example 1 to obtain 0.68 g of 6-ethoxy-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridine-2-amine, at 98.0% purity, as a yellow viscous liquid, yield of 28.2%. GC-MS (M+) (EI, 70 eV, m/z) calc: 342. found: 342. 1H NMR (CDCl3/TMS, 300 MHz) δ (ppm) 1.100 (t, J=6.9 Hz, 3H, CH3), 1.322 (t, J=6.9 Hz, 3H, CH3), 3.189 (q, J=6.9 Hz, 2H, CH2), 4.295 (q, J=6.9 Hz, 2H, CH2), 4.754 (s, 2H, CH2), 6.108 (d, J=9.0 Hz, 1H, Py H), 7.397 (s, 1H, Thiazole H), 8.084 (d, J=9.0 Hz, 1H, Py H).
Workup
- additiontreated
Sources & evidence
- ORD record
- ord-04ede71993c048d18ad9dd3e72354e47
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09386769B2
Reaction notes
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