Acetyl chloride → HCID 86640028, compound

HRID 452624Notes

Reaction equation

HRID 452624 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[C:12]([C:14]([NH:16][NH2:17])=[O:15])[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:19](N(CC)CC)[CH3:20].C(Cl)(=O)C.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>O1CCCC1.O>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1[CH:13]=[C:12]([C:14]2[O:15][C:19]([CH3:20])=[N:17][N:16]=2)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2×HCID 86640026Tert-butyl [4-(hydrazinocarbonyl)-2-pyridyl]carbamate

Product 1

HCID 86640028HCID 86640028, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl[4-(hydrazinocarbonyl)-2-pyridyl]carbamate (1.01 g, 4.0 mmol) and triethylamine (0.832 mL, 6.0 mmol) in tetrahydrofuran (20 mL) was added acetyl chloride (0.341 mL, 4.8 mmol) under ice-cooling, and the resulting mixture was stirred at room temperature for 1 hr. To this reaction mixture were added triethylamine (2.77 mL, 20 mmol) and p-toluenesulfonyl chloride (1.53 g, 8.0 mmol), and the resulting mixture was heated under reflux for 20 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 purified by basic silica gel column chromatography (tetrahydrofuran), and washed with diethyl ether/methanol to give the title compound (448 mg, yield 41%) as pale-brown crystals.

Workup

  1. temperaturecooling
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux for 20 hr
  4. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by basic silica gel column chromatography (tetrahydrofuran)
  9. washwashed with diethyl ether/methanol

Sources & evidence

ORD record
ord-3a0f93ce9c3949408aec822b4c1c0f19
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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