Ethyl Acetate → HCID 12044044, compound

HRID 1840533Notes

Reaction equation

HRID 1840533 reaction equation
Cl.[C:2]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][C:10]2=[O:15])=[CH:6][CH:5]=1)#[N:3].[Cl:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([S:29](Cl)(=[O:31])=[O:30])[CH:23]=[CH:22]2.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>O>[Cl:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH:25]=[C:24]([S:29]([N:12]1[CH2:13][CH2:14][N:9]([CH2:8][C:7]3[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:17][CH:16]=3)[C:10](=[O:15])[CH2:11]1)(=[O:31])=[O:30])[CH:23]=[CH:22]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 106351296-Chloronaphthalene-2-sulfonyl chlorideHCID 23447422HCID 23447422, compound

Product 1

HCID 12044044HCID 12044044, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(4-cyanobenzyl)-2-piperazinone hydrochloride (201 mg), 6-chloronaphthalene-2-sulfonyl chloride (205 mg), sodium carbonate (254 mg), ethyl acetate (10 ml) and water (5 ml) was stirred at room temperature for 2 hours. The organic layer was separated, washed with saturated brine, dried (MgSO4) and concentrated. The residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2) to give pale pink crystals of the title compound (239 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified with silica gel column chromatography (hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-95eaa12f67cf4b74a961e9859adbdeca
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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