6-chloro-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridin-2-amine → 6-propargyloxy-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridine-2-amine

HRID 1050714Notes

Reaction equation

HRID 1050714 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].[Na].Cl[C:7]1[N:12]=[C:11]([N:13]([CH2:16][C:17]2[S:21][C:20]([Cl:22])=[N:19][CH:18]=2)[CH2:14][CH3:15])[C:10]([N+:23]([O-:25])=[O:24])=[CH:9][CH:8]=1>ClCCl>[CH2:1]([O:4][C:7]1[N:12]=[C:11]([N:13]([CH2:16][C:17]2[S:21][C:20]([Cl:22])=[N:19][CH:18]=2)[CH2:14][CH3:15])[C:10]([N+:23]([O-:25])=[O:24])=[CH:9][CH:8]=1)[C:2]#[CH:3]

Participants

4

Reactant 2

HCID 1178760026-chloro-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridin-2-amineHCID 131736087Sodium propargyl alcohol

Product 1

HCID 1178764416-propargyloxy-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridine-2-amineYield 23.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.52 g of sodium propargyl alcohol and 10 mL of anhydrous dichloromethane were added into a 100 mL three-necked flask equipped with a magnetic stirrer, a condenser and a drying tube, under stirring at room temperature, 1.15 g of 6-chloro-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridin-2-amine, prepared according to the example 1, in 5 mL of dichloromethane was added dropwise. After that, the reaction mixture was stirred at room temperature for 1 to 2 hours, and then stirred at reflux temperature for 2 to 5 hours. After cooling down to the room temperature, the reaction mixture was treated by the method according to example 1 to obtain 0.29 g of 6-propargyloxy-N-((2-chlorothiazole-5-yl)methyl)-N-ethyl-3-nitropyridine-2-amine, as a viscous yellow-green solid in a yield of 23.8%. GC-MS (M+) (EI, 70 eV, m/z) calc: 352. found: 352. 1H NMR (CDCl3/TMS, 300 MHz) δ (ppm): (CDCl3) 1.212 (t, J=7.2 Hz, 3H, CH3), 2.497 (t, J=2.4 Hz, 1H, CH), 3.265 (q, J=7.2 Hz, 2H, CH2), 4.850 (s, 2H, CH2), 4.969 (s, 2H, CH2), 6.263 (d, J=8.7 Hz, 1H, Py H), 7.489 (s, 1H, Thiazole-H), 8.182 (d, J=8.7 Hz, 1H, Py H).

Workup

  1. customequipped with a magnetic stirrer, a condenser and a drying tube
  2. additionwas added dropwise
  3. stirringAfter that, the reaction mixture was stirred at room temperature for 1 to 2 hours
  4. stirringstirred
  5. temperatureat reflux temperature for 2 to 5 hours
  6. temperatureAfter cooling down to the room temperature
  7. additionthe reaction mixture was treated by the method

Sources & evidence

ORD record
ord-90dc5ae8084f45ce8c7431dc61c7c1c5
Source dataset
uspto-grants-2016_07
Patent number
US09386769B2

Reaction notes

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