Sodium ethoxide → Ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate

HRID 1838951Notes

Reaction equation

HRID 1838951 reaction equation
Cl[C:2]1[N:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH3:23])[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[O-:24][CH2:25][CH3:26].[Na+]>C(O)C>[CH2:25]([O:24][C:2]1[N:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:21][CH2:20][N:19]([CH2:22][CH3:23])[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:26]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 22052238Ethyl 2-chloro-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate

Product 1

HCID 10109777Ethyl 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoateYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of Ethyl 2-chloro-5-(4-ethyl-1-piperazinylsulfonyl)nicotinoate (36.1 g, 0.1 mol) in ethanol (180 mL) was cooled to 10° C. with stirring. Sodium ethoxide (10.2 g, 0.15 mol) was added portionwise keeping the temperature below 20° C. The reaction mixture was then stirred at ambient temperature for 18 hours. The precipitate was filtered off and water (180 mL) added to the filtrate. The filtrate was then heated to 40° C. for 1 hour. Ethanol (180 mL) was then distilled off at ambient pressure and the remaining aqueous solution allowed to cool to ambient temperature. The precipitated product was then filtered off, washed with water and dried under vacuo at 50° C. to afford the title compound (12.6 g, 34%) as a light brown solid. M.p. 66-68° C. δ (CDCl3): 1.04 (3H, t), 1.39 (3H, t), 1.45 (3H, t), 2.41 (2H, q), 2.52 (4H, m), 3.08 (4H, m), 4.38 (2H, q), 2.57 (2H, q), 8.38 (1H, d), 8.61 (1H, d). m/z (Found:372 [M+H]+, 100%. C16H26N3O5S requires 372.46).

Workup

  1. customthe temperature below 20° C
  2. stirringThe reaction mixture was then stirred at ambient temperature for 18 hours
  3. filtrationThe precipitate was filtered off
  4. additionwater (180 mL) added to the filtrate
  5. distillationEthanol (180 mL) was then distilled off at ambient pressure
  6. temperatureto cool to ambient temperature
  7. filtrationThe precipitated product was then filtered off
  8. washwashed with water
  9. customdried under vacuo at 50° C.

Sources & evidence

ORD record
ord-a95f87131a7945b4a20db159c0b0e083
Source dataset
uspto-grants-2004_01
Patent number
US06677335B1

Reaction notes

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