Water → HCID 12074212, compound

HRID 1369397Notes

Reaction equation

HRID 1369397 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1.[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.C(Cl)Cl>[N+:17]([C:4]1[CH:3]=[C:2]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:7]=[CH:6][C:5]=1[S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9])([O-:19])=[O:18]

Participants

7

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 11430Potassium CarbonateHCID 378892HCID 378892, compound

Product 1

HCID 12074212HCID 12074212, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-fluoro-2-nitro-1-(phenylsulfonyl) benzene (1.0 g, 3.6 mmol), piperazine (0.37 g, 4.3 mmol), and potassium carbonate (0.79 g, 5.7 mmol) is stirred in 35 mL of acetonitrile overnight at reflux. The mixture is cooled to rt and 35 mL of water and CH2Cl2 are added. The layers are separated and the aqueous layer extracted with CH2Cl2 (3×35 mL). The combined organics are dried over MgSO4, filtered, and concentrated. Purification via flash column chromatography (15% MeOH/CH2Cl2) gives 1.1 g (92%) of title compound as a solid, mp 180-182° C.

Workup

  1. temperatureat reflux
  2. customThe layers are separated
  3. extractionthe aqueous layer extracted with CH2Cl2 (3×35 mL)
  4. dry with materialThe combined organics are dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via flash column chromatography (15% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-975cd5d7bb8b4c5f89fcd9202c08cfed
Source dataset
uspto-grants-2003_06
Patent number
US06579870B2

Reaction notes

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