Acetyl chloride → HCID 68664228, compound

HRID 452604Notes

Reaction equation

HRID 452604 reaction equation
[CH3:1][O: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.[C:29](Cl)(=[O:31])[CH3:30]>O1CCCC1.C(OCC)(=O)C>[C:29]([NH:21][NH:20][C:18]([C:15]1[CH:16]=[CH:17][C:12]2[O:11][CH:10]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:13]=2[CH:14]=1)=[O:19])(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 68663192HCID 68663192, compound

Product 1

HCID 68664228HCID 68664228, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(4-methoxyphenyl)-1-benzofuran-5-carbohydrazide (565 mg, 2.00 mmol) and triethylamine (0.418 mL, 3.00 mmol) in tetrahydrofuran (30 mL) was added acetyl chloride (0.213 mL, 3.00 mmol) at room temperature, and the resulting mixture was stirred for 30 min. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was washed with hexane/ethyl acetate (1/1) to give the title compound (613 mg, yield 94%) as colorless crystals.

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe residue was washed with hexane/ethyl acetate (1/1)

Sources & evidence

ORD record
ord-b6edbab0ad624da08986e0962f6baf24
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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