5-Phenyl-2-pyridinamine → 2,6-Dichloro-N-[(5-phenylpyridin-2-yl)carbamoyl]benzamide

HRID 1995608Notes

Reaction equation

HRID 1995608 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[C:14]1([C:20]2[CH:21]=[CH:22][C:23]([NH2:26])=[N:24][CH:25]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl:13])[C:3]=1[C:4]([NH:6][C:7]([NH:26][C:23]1[CH:22]=[CH:21][C:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:25][N:24]=1)=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 1050975-Phenyl-2-pyridinamineHCID 129127392,6-Dichlorobenzoyl isocyanate

Product 1

HCID 132426492,6-Dichloro-N-[(5-phenylpyridin-2-yl)carbamoyl]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,6-Dichlorobenzoyl isocyanate (1.5 grams) in a small amount of dichloromethane was added to a solution of 5-phenyl-2-pyridylamine (1.0 gram) in 15 ml dichloromethane. After refluxing for about 5 minutes a precipitate formed. Following this, the reaction mixture was stirred at room temperature, cooled, and then the precipitate was filtered and recrystallized from ethanol, yield 1.8 grams. The identity of the final product was confirmed by NMR, m.p. 221°-231° C.

Workup

  1. temperatureAfter refluxing for about 5 minutes a precipitate
  2. customformed
  3. temperaturecooled
  4. filtrationthe precipitate was filtered
  5. customrecrystallized from ethanol, yield 1.8 grams

Sources & evidence

ORD record
ord-84dc689e58e8459c8a05a6500dd83b5d
Source dataset
uspto-grants-1983_09
Patent number
US04405552

Reaction notes

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