4-Phenylbenzoyl chloride → N-(5-Chloropyridin-2-yl)-2-(4-phenylbenzoylamino)benzamide

HRID 988608

Reaction equation

HRID 988608 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH2:16])=[N:6][CH:7]=1.[C:18]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:23]=[CH:22][C:21]([C:24](Cl)=[O:25])=[CH:20][CH:19]=1>ClCCl.N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:24](=[O:25])[C:21]2[CH:22]=[CH:23][C:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:19][CH:20]=2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 841514-Phenylbenzoyl chlorideHCID 219063812-amino-N-(5-chloropyridin-2-yl)benzamide

Product 1

HCID 21906587N-(5-Chloropyridin-2-yl)-2-(4-phenylbenzoylamino)benzamideYield 94%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(5-chloropyridin-2-yl)-2-aminobenzamide(0.247 g, 1 mmol) in dichloromethane (10 mL) and pyridine (0.5 mL) was added a solution of 4-biphenylcarbonyl chloride (0.217 g, 1 mmol) in dichloromethane (5 mL). After stirring overnight the solvent was removed in vacuo. The residue was partitioned between ethyl acetate (50 mL) and water (25 mL). Separate the layers and wash the organic layer with water (2×10 mL), saturated sodium bicarbonate (2×20 mL), hydrochloric acid (0.2 N, 1×20 mL). Dried over MgSO4, filtered and concentrated in vacuo. The residue was then purified by RPHPLC (30% ethyl acetate/hexane) to give 0.4 g (94%) of pure product.

Workup

  1. customwas removed in vacuo
  2. customThe residue was partitioned between ethyl acetate (50 mL) and water (25 mL)
  3. customSeparate the layers
  4. washwash the organic layer with water (2×10 mL), saturated sodium bicarbonate (2×20 mL), hydrochloric acid (0.2 N, 1×20 mL)
  5. dry with materialDried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by RPHPLC (30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c097e432feb545178e2ce278c61c05b1
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Linked notes

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