Benzoyl chloride, 3-chloro- → N-Methyl-N-(4-o-tolyl-pyridin-3-yl)-3-chloro-benzamide

HRID 877961Notes

Reaction equation

HRID 877961 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[CH3:11][NH:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25].CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:11][N:12]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH3:25])[C:5](=[O:6])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=1

Participants

5

Reactant 3

HCID 69252Benzoyl chloride, 3-chloro-HCID 81531DiisopropylethylamineHCID 18403336N-methyl-4-o-tolylpyridin-3-amine

Product 1

HCID 60196993N-Methyl-N-(4-o-tolyl-pyridin-3-yl)-3-chloro-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chlorobenzoyl chloride (30 mg, 0.17 mmol, CAS RN 618-46-2) was added to a solution of methyl-(4-o-tolyl-pyridin-3-yl)-amine (20 mg, 0.10 mmol, example 1, intermediate a) and DIPEA (30 μL, 0.17 mmol) in CH2Cl2 (1 mL). The reaction mixture was stirred overnight and then loaded directly onto a silica gel column and eluted with 50% EtOAc in n-hexane to yield the title product as a waxy solid (12 mg, 36%). MS (ESI): m/z=337.0 [M+H]+.

Workup

  1. washeluted with 50% EtOAc in n-hexane

Sources & evidence

ORD record
ord-13b7bb136e7344648ea4ca11aefce137
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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