Chloroform → HCID 18315487, compound

HRID 276021Notes

Reaction equation

HRID 276021 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=[O:21])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[C:12]([NH2:20])[CH:11]=1.[CH2:22]1[O:32][C:31]2[CH:30]=[CH:29][C:26]([CH2:27]Cl)=[CH:25][C:24]=2[O:23]1.C(=O)([O-])O.[Na+].C(Cl)(Cl)Cl>CN(C)C=O.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9](=[O:21])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:19])[CH3:18])=[C:12]([NH:20][CH2:27][C:26]2[CH:29]=[CH:30][C:31]3[O:32][CH2:22][O:23][C:24]=3[CH:25]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 516892Sodium BicarbonateHCID 18315403HCID 18315403, compound

Product 1

HCID 18315487HCID 18315487, compoundYield 41.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 0.80 g of N-(2-pyridylmethyl)-4-acetylamino-3-aminobenzamide in 10 ml of N,N-dimethylformamide were added 0.962 g of 3,4-methylenedioxybenzyl chloride and 0.710 g of sodium hydrogencarbonate, and the mixture was stirred at 80° C. for 4 hours. Chloroform and water were added to the reaction solution, and the chloroform extraction was conducted. The organic layer was washed with water, concentrated, and purified through silica-gel column chromatography (eluent: a mixture of ethyl acetate and methanol at a ratio of 9:1) to give 0.49 g of N-(2-pyridylmethyl)-4-acetylamino-3-(3,4-methylenedioxybenzylamino)benzamide.

Workup

  1. extractionthe chloroform extraction
  2. washThe organic layer was washed with water
  3. concentrationconcentrated
  4. custompurified through silica-gel column chromatography (eluent
  5. additiona mixture of ethyl acetate and methanol at a ratio of 9:1)

Sources & evidence

ORD record
ord-54a3ba54c2c44e00bd23f4e5036e0696
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

Loading…