Water → HCID 12074212, compound

HRID 1356541Notes

Reaction equation

HRID 1356541 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-a8114cadb70a41a2a10ba3c5d3bc328d
Source dataset
uspto-grants-2003_07
Patent number
US06586592B2

Reaction notes

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