Water → HCID 12074220, compound

HRID 1369399Notes

Reaction equation

HRID 1369399 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].F[C:14]1[CH:19]=[CH:18][C:17]([S:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:16]([N+:27]([O-:29])=[O:28])[CH:15]=1.O>C(#N)C.C(Cl)Cl>[N+:27]([C:16]1[CH:15]=[C:14]([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[CH:19]=[CH:18][C:17]=1[S:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([O-:29])=[O:28]

Participants

7

Reactant 4

HCID 962WaterHCID 4837PiperazineHCID 11430Potassium CarbonateHCID 378891HCID 378891, compound

Product 1

HCID 12074220HCID 12074220, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of piperazine (1.0 g, 12 mmol) and potassium carbonate (2.0 g, 14 mmol) in 80 mL of dry acetonitrile is added 4-fluoro-2-nitro-1-(phenylsulfanyl) benzene (2, EXAMPLE 1, step 1, 2.7 g, 9.5 mmol). The mixture is allowed to stir overnight at rt. Water and CH2Cl2 (80 mL each) are added and the layers separated. The aqueous layer is extracted with CH2Cl2 (3×50 mL). The combined organic layers are dried over MgSO4, filtered, and concentrated. Purification via column chromatography (50% EtOAc/hexane) gives 1.6 g (47%) of the title compound as a red oil.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer is extracted with CH2Cl2 (3×50 mL)
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification via column chromatography (50% EtOAc/hexane)

Sources & evidence

ORD record
ord-834eddb1eceb41168696cdbbb58f613b
Source dataset
uspto-grants-2003_06
Patent number
US06579870B2

Reaction notes

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