Hydrochloric Acid → Ethyl 2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]benzoate

HRID 1581738Notes

Reaction equation

HRID 1581738 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)(=[O:15])=[O:14])=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].Cl.[CH2:24](O)[CH3:25]>>[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]2)(=[O:15])=[O:14])=[CH:9][C:5]=1[C:6]([O:8][CH2:24][CH3:25])=[O:7])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 121348652-Ethoxy-5-(4-methylpiperazine-1-sulfonyl)benzoic acid

Product 1

HCID 22052241Ethyl 2-ethoxy-5-[(4-methylpiperazin-1-yl)sulfonyl]benzoateYield 45.5%

Procedure

To a suspension of 2-ethoxy-5-(4-methyl-1-piperazinylsulfonyl)benzoic acid (16.4 g, 0.05 mol, see EP 812 845) in ethanol (160 mL) was added concentrated hydrochloric acid (12.5 mL, 0.15 mol), which gave a solution on stirring. The solution was heated to reflux for 25 hours and then allowed to cool. It was concentrated under vacuum to give an orange oil which gave crystals on cooling. These were collected by filtration to give 13.7 g of crude product, which was purified by recrystallisation in acetonitrile to give 8.1 g of product as fine white crystals (45.5%).

Workup

  1. customgave a solution
  2. temperatureThe solution was heated
  3. temperatureto reflux for 25 hours
  4. temperatureto cool
  5. concentrationIt was concentrated under vacuum
  6. customto give an orange oil which
  7. customgave crystals
  8. temperatureon cooling
  9. filtrationThese were collected by filtration
  10. customto give 13.7 g of crude product, which
  11. customwas purified by recrystallisation in acetonitrile

Sources & evidence

ORD record
ord-59422540d05f4fd483887aa29be175f8
Source dataset
uspto-grants-2004_05
Patent number
US06730786B2

Reaction notes

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