Ethanol → HCID 22272564, compound

HRID 230479Notes

Reaction equation

HRID 230479 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:7]=1.[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.CCO>CN(C=O)C.[Cl-].[Na+].O>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:2]2[CH:3]=[CH:4][C:5]([N+:13]([O-:15])=[O:14])=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:7]=2)[CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 702EthanolHCID 531671-MethylpiperazineHCID 22272570HCID 22272570, compound

Product 1

HCID 22272564HCID 22272564, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
20 °C

Procedure

N-(5-fluoro-2-nitrophenyl)methanesulfonamide (1.33 g, 5.68 mmol) was dissolved in DMF (10 mL) and N-methylpiperazine (2.00 g, 20 mmol) was added. The reaction mixture was stirred at 20° C. for 1 h, and then heated with a heat gun for 5 min to reach boiling of DMF (150° C.), then left stirring for another hour. The reaction mixture was then poured into brine and extracted with toluene (10 mL×2), EtOAc (20 mL×2) and CH2Cl2 (20 mL×2), NaHCO3 was then added to the water phase and then the water phase was extracted with CH2Cl2 (20 mL×2). The organic phases were combined and dried (MgSO4) and concentrated to give a semi solid. EtOH was added and left over night and then filtered off to give 1.503 g (4.78 mmol) in 84% yield. MS (posES-FIA) m/z=found: 315; Calc M=314.10; Anal (C)2H18N4O4S), C, H, N, S.

Workup

  1. temperatureheated with a heat gun for 5 min
  2. waitleft
  3. stirringstirring for another hour
  4. extractionextracted with toluene (10 mL×2), EtOAc (20 mL×2) and CH2Cl2 (20 mL×2), NaHCO3
  5. additionwas then added to the water phase
  6. extractionthe water phase was extracted with CH2Cl2 (20 mL×2)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto give a semi solid
  10. waitleft over night
  11. filtrationfiltered off
  12. customto give 1.503 g (4.78 mmol) in 84% yield

Sources & evidence

ORD record
ord-a4bcb3cf628e4256a68c707d5bccca90
Source dataset
uspto-grants-2009_07
Patent number
US07566715B2

Reaction notes

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