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

HRID 1980311Notes

Reaction equation

HRID 1980311 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-12487ae47e154003b1875d6336e48123
Source dataset
uspto-grants-1985_04
Patent number
US04508722

Reaction notes

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