Water → HCID 15923531, compound

HRID 2187057Notes

Reaction equation

HRID 2187057 reaction equation
N[C:2]1[N:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)=[O:5].ClC(O[CH2:24][CH3:25])=O.[OH2:26]>N1C=CC=CC=1>[O:26]=[C:18]1[N:6]([CH2:7][C:8]2[CH:9]=[CH:10][C:11]([O:14][CH3:15])=[CH:12][CH:13]=2)[C:4](=[O:5])[C:3]2[C:2](=[CH:24][CH:25]=[CH:17][CH:16]=2)[NH:19]1

Participants

5

Reactant 3

HCID 962WaterHCID 10928Ethyl chloroformateHCID 224497462-Amino-N-[(4-methoxyphenyl)methyl]-3-pyridinecarboxamide

Product 1

HCID 15923531HCID 15923531, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(Method 2) 2-Amino-N-(methoxybenzyl)benzamide (23.6 g) was dissolved in pyridine (150 ml) and treated dropwise with ethyl chloroformate (10.6 ml) with stirring and cooling on ice. The reaction mixture was stirred at room temperature for 8 hours, and then heated under reflux for 18.5 hours. After cooling followed by pouring into an iced water followed by the treatment similar to that in Method 1, the title compound (25.5 g, 98%) was obtained as a colorless crystal.

Workup

  1. temperaturecooling on ice
  2. stirringThe reaction mixture was stirred at room temperature for 8 hours
  3. temperatureheated
  4. temperatureunder reflux for 18.5 hours
  5. temperatureAfter cooling

Sources & evidence

ORD record
ord-1a167e001c3d459791c43ea6b54345dc
Source dataset
uspto-grants-2002_06
Patent number
US06407116B1

Reaction notes

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