Thionyl Chloride → HCID 22120448, compound

HRID 1274166Notes

Reaction equation

HRID 1274166 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:12][C:13]([NH:15][C:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23](O)=[O:24])=[CH:21][CH:20]=1)([CH3:18])[CH3:17])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN(C)C=O.ClCCl>[CH2:5]([O:12][C:13]([NH:15][C:16]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([Cl:3])=[O:24])=[CH:21][CH:20]=1)([CH3:18])[CH3:17])=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 221204494-[1-Methyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]benzoic acid

Product 1

HCID 22120448HCID 22120448, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.21 ml) and dimethylformamide (2 drops) were added to a solution of 4-(1-benzyloxycarbonylamino-1-methylethyl)-benzoic acid (780 mg) in dichloromethane (10 ml), and the mixture was refluxed under heating for 1 hour. After the reaction, the solvent was evaporated under reduced pressure to give 4-(1-benzyloxycarbonylamino-1-methylethyl)benzoyl chloride as crystals. Then, the crystals were dissolved in acetonitrile (10 ml), and the solution was dropwise added to a solution of 4-aminopyridine (195 mg) and diisopropylethylamine (0.5 ml) in acetonitrile (10 ml) under ice-cooling. The mixture was stirred at room temperature for 5 hours. After the reaction, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried. The solvent was evaporated under reduced pressure, and the obtained crystals were recrystallized from ethyl acetate-hexane to give 750 mg of N-(4-pyridyl)-4-(1-benzyloxycarbonylamino-1-methylethyl)benzamide.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 1 hour
  3. customAfter the reaction
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6e7114aff7bf4c5fbfec687f88630fa5
Source dataset
uspto-grants-2000_12
Patent number
US06156766

Reaction notes

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