Water → HCID 15232186, compound

HRID 1492530Notes

Reaction equation

HRID 1492530 reaction equation
[NH2:1][CH:2]([C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1)[CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.C(N(CC)CC)C.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1.O>ClCCl>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([S:34]([NH:1][CH:2]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH2:3][C:4]2[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=2)(=[O:36])=[O:35])=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 18950757HCID 18950757, compound

Product 1

HCID 15232186HCID 15232186, compoundYield 34.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.19 g (0.74 mM) of methyl 4-[2-amino-2-(3-pyridyl)ethyl]benzoate in 10ml of dichloromethane in solution were added triethylamine (0.13 ml, 0.9 mM) and p-chlorobenzenesulfonyl chloride (0.19 g, 0.9 mM), and stirred overnight at room temperature. After completion of the reaction, water was poured into the reaction mixture, followed by extraction of dichloromethane. The organic phase was then washed in saturated aqueous sodium chloride solution and dried over magnesium sulfate, to distill off the solvent. The residue was subjected to chromatography on a silica gel column, which was then eluted with chloroform to yield 0.11 g of methyl 4-[2-(4-chlorobenzenesulfonamido)-2-(3-pyridyl)ethyl]benzoate. The spectrometric data thereof supports the structure of [26] as follows.

Workup

  1. additionwas poured into the reaction mixture
  2. extractionfollowed by extraction of dichloromethane
  3. washThe organic phase was then washed in saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. distillationto distill off the solvent
  6. washwas then eluted with chloroform

Sources & evidence

ORD record
ord-75008bebbcea45d8a2415a4802009b33
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

Loading…