Pyridine → HCID 22010900, compound

HRID 323138Notes

Reaction equation

HRID 323138 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([N:8]([CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:9]2[CH:16]=[CH:15][C:12]([O:13][CH3:14])=[CH:11][CH:10]=2)=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:30]1([CH3:39])[C:31]([C:36](Cl)=[O:37])=[CH:32][CH:33]=[CH:34][CH:35]=1>ClCCl>[CH:17]1([N:8]([C:6](=[O:7])[C:5]2[CH:22]=[CH:23][C:2]([NH:1][C:36](=[O:37])[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[CH3:39])=[CH:3][CH:4]=2)[C:9]2[CH:16]=[CH:15][C:12]([O:13][CH3:14])=[CH:11][CH:10]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 702762-Methylbenzoyl chlorideHCID 22010923HCID 22010923, compound

Product 1

HCID 22010900HCID 22010900, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(4-aminobenzoyl)-N-cyclopentyl-p-anisidine (870 mg) and pyridine (443 mg) in dichloromethane (20 ml) was added o-toluoyl chloride (868 mg) at 0° C. Then the mixture was stirred for 3 hours at ambient temperature. The reaction mixture was concentrated and diluted with ethyl acetate and the solution was washed with water, IN-hydrochloric acid and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography (SiO2 20 g, ethyl acetate:n-hexane=1:2). The eluent was concentrated and triturated with diethyl ether to give N-cyclopentyl-N-[4-(2-methylbenzoylamino)benzoyl]-p-anisidine (750 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washthe solution was washed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography (SiO2 20 g, ethyl acetate:n-hexane=1:2)
  8. concentrationThe eluent was concentrated
  9. customtriturated with diethyl ether

Sources & evidence

ORD record
ord-fac8e847a20246f993ae98d06c012535
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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