Oxalyl chloride → 4-Chloro-3-(3,5-dichloro-pyridin-2-yl)benzoyl chloride

HRID 1485962Notes

Reaction equation

HRID 1485962 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[C:11]1[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=1.C(Cl)(=O)C([Cl:22])=O>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:22])=[O:7])=[CH:4][C:3]=1[C:11]1[C:16]([Cl:17])=[CH:15][C:14]([Cl:18])=[CH:13][N:12]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 686040024-Chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoic acid

Product 1

HCID 866425734-Chloro-3-(3,5-dichloro-pyridin-2-yl)benzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoic acid (100 mg, 0.33 mmol) in dry DCM (1 mL), was added DMF (1 drop) followed by addition of oxalyl chloride (35 μL, 0.40 mmol) slowly. The mixture was stirred for 2.5 hrs, then concentrated to yield 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoyl chloride, which was dissolved in DCM (1 mL). 2-Methylamino-phenol (45 mg, 0.36 mmol) was added followed by the slow addition of diisopropylethylamine (88 μL, 0.5 mmol). The mixture was stirred at room temperature for 12 hrs, concentrated and purified by preparative TLC (DCM/MeOH=9/1) followed by preparative LCMS to yield 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-N-(2-hydroxy-phenyl)-N-methyl-benzamide 19-1. MS (M+H)+: 409.0, tR=7.55 min (method 2)

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-e03b9317419d4b33a11d261db59a9fa8
Source dataset
uspto-grants-2016_08
Patent number
US09422310B2

Reaction notes

Loading…