Acetonitrile → HCID 23154178, compound

HRID 639443Notes

Reaction equation

HRID 639443 reaction equation
C(#N)C.[O:4]=[S:5]1(=[O:16])[CH2:9][CH2:8][CH2:7][N:6]1[CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([N:28]2[C:32]3[CH:33]=[CH:34][C:35]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:36][C:31]=3[N:30]=[C:29]2Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C>C(OCC)(=O)C.O>[O:16]=[S:5]1(=[O:4])[CH2:9][CH2:8][CH2:7][N:6]1[CH:10]1[CH2:15][CH2:14][N:13]([C:29]2[N:28]([S:25]([C:22]3[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=3)(=[O:27])=[O:26])[C:32]3[CH:33]=[CH:34][C:35]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[CH:36][C:31]=3[N:30]=2)[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 23154167HCID 23154167, compoundHCID 53256087688020-17-9

Product 1

HCID 23154178HCID 23154178, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the acetonitrile solution (3 mL) containing 4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)piperidine (136 mg) were added 1-(4-methoxyphenylsulfonyl)-2-chloro-5-phenylbenzimidazole (340 mg) and diisopropylethylamine (0.41 mL), followed by stirring at room temperature for 16 hrs. The reaction mixture was diluted with ethyl acetate and water, and the organic layer was washed with an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was separated and purified on a collective thin-layer chromatograph (ethyl acetate) to give the title compound (157 mg).

Workup

  1. washthe organic layer was washed with an aqueous saturated sodium chloride solution
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was separated
  5. custompurified on a collective thin-layer chromatograph (ethyl acetate)

Sources & evidence

ORD record
ord-a76bd133696a42cbab395e41794e2c15
Source dataset
uspto-grants-2010_04
Patent number
US07691860B2

Reaction notes

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