Water → 5-Chloro-2-(4-fluorobenzoylamino)-N-(5-chloropyridin-2-yl)-benzamide

HRID 1373698Notes

Reaction equation

HRID 1373698 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1)=[O:5].[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.O>C(Cl)Cl.N1C=CC=CC=1>[Cl:18][C:15]1[CH:16]=[CH:17][C:2]([NH:1][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][C:20]([F:19])=[CH:21][CH:22]=2)=[C:3]([CH:14]=1)[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1)=[O:5]

Participants

6

Reactant 3

HCID 962WaterHCID 678794-Fluorobenzoyl chlorideHCID 219064182-Amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide

Product 1

HCID 210753305-Chloro-2-(4-fluorobenzoylamino)-N-(5-chloropyridin-2-yl)-benzamideYield 79.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-amino-5-chloro-N-(5-chloropyridin-2-yl)benzamide (2.82 g, 10 mmol) in methylene chloride (100 mL) and pyridine (3 mL) was added 4-fluorobenzoyl chloride (1.42 mL, 12 mmol) dropwise at 0° C. The reaction mixture was warmed to room temperature and stirred overnight. Water (50 mL) was added; and the mixture was stirred for 30 min before the solids were filtered, washed with saturated sodium bicarbonate (30 mL), water (30 mL), and ether (50 mL), and dried under vacuum to provide the product (3.2 g, 79%) pure enough to use in the next step.

Workup

  1. stirringand the mixture was stirred for 30 min before the solids
  2. filtrationwere filtered
  3. washwashed with saturated sodium bicarbonate (30 mL), water (30 mL), and ether (50 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-5ce59db29d284ea39a00c4d3edab87da
Source dataset
uspto-grants-2007_01
Patent number
US07163938B2

Reaction notes

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