Acetic Acid → HCID 68663473, compound

HRID 452747Notes

Reaction equation

HRID 452747 reaction equation
[C:1](O)(=O)C.[CH3:5][S:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]3[CH:19]=[C:20]([C:23]([NH:25][NH2:26])=[O:24])[CH:21]=[CH:22][C:17]=3[N:16]=[CH:15]2)=[CH:10][CH:9]=1)=[O:7].CN(C)C=O.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O1CCCC1.N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:5][S:6]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:18]3[CH:19]=[C:20]([C:23]4[O:24][CH:1]=[N:26][N:25]=4)[CH:21]=[CH:22][C:17]=3[N:16]=[CH:15]2)=[CH:10][CH:9]=1)=[O:7]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 73974-Toluenesulfonyl chlorideHCID 68664090HCID 68664090, compound

Product 1

HCID 68663473HCID 68663473, compoundYield 3.8%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of acetic acid (57 μl, 1.00 mmol) and N,N′-carbonyldiimidazole (195 mg, 1.20 mmol) in tetrahydrofuran (20 mL) was stirred at room temperature for 1 hr. To this reaction mixture were added 1-[4-(methylsulfinyl)phenyl]-1H-benzimidazole-6-carbohydrazide (314 mg, 1.00 mmol) and N,N-dimethylformamide (5 mL), and the resulting mixture was stirred overnight. To this reaction mixture was added a solution of p-toluenesulfonyl chloride (381 mg, 2.00 mmol) in pyridine (5 mL), and the resulting mixture was stirred at 80° C. for 24 hr. After cooling, the reaction mixture was diluted with chloroform, washed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=4/1-0/1) and recrystallized from hexane/ethyl acetate to give the title compound (12 mg, yield 3.8%) as colorless crystals.

Workup

  1. stirringthe resulting mixture was stirred at 80° C. for 24 hr
  2. temperatureAfter cooling
  3. washwashed with 1M hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=4/1-0/1)
  7. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-e86a4db125e349b7873414e090354639
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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