Chloroform → HCID 18681145, compound

HRID 1276880Notes

Reaction equation

HRID 1276880 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]([O:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=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][CH2:34][C:33]2[CH:36]=[CH:37][C:30]([O:29][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:31][CH:32]=2)[CH:11]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 700424-Benzyloxybenzyl chlorideHCID 516892Sodium BicarbonateHCID 18315403HCID 18315403, compound

Product 1

HCID 18681145HCID 18681145, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °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 1.31 g of 4-benzyloxybenzyl chloride and 1.18 g of sodium hydrogencarbonate, and the mixture was stirred at 90° C. for 2 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 to give 0.434 g of N-(2-pyridylmethyl)-4-acetylamino-3-(4-benzyloxybenzylamino)benzamide.

Workup

  1. extractionthe chloroform extraction
  2. washThe organic layer was washed with water
  3. concentrationconcentrated
  4. custompurified through silica-gel column chromatography

Sources & evidence

ORD record
ord-7bfef5bfeac5404e803f2b701e9b180e
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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