Water → HCID 178503119, compound

HRID 452815Notes

Reaction equation

HRID 452815 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH:14]=[C:15]([C:18]([NH:20][NH2:21])=[O:19])[CH:16]=[CH:17][C:12]=3[O:11][CH:10]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.O.CN(C)[CH:32]=[O:33]>>[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:13]3[CH:14]=[C:15]([C:18]4[O:19][C:32]([OH:33])=[N:21][N:20]=4)[CH:16]=[CH:17][C:12]=3[O:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 8471TriethylamineHCID 44480698HCID 44480698, compound

Product 1

HCID 178503119HCID 178503119, compoundYield 74%

Procedure

To a solution of 3-[4-(methylthio)phenyl]-1-benzofuran-5-carbohydrazide (0.25 g, 0.83 mmol) and triethylamine (0.17 mL, 1.25 mmol) in N,N-dimethylformamide (5 mL) was added N,N′-carbonyldiimidazole (0.27 g, 1.68 mmol) at 0° C., and the resulting mixture was stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate/tetrahydrofuran. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane/ethyl acetate to give the title compound (0.20 g, yield 74%) as colorless crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-4accaf8099604980883531d01c78632a
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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