Water → HCID 15232188, compound

HRID 1492536Notes

Reaction equation

HRID 1492536 reaction equation
[NH2:1][CH:2]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1.C(N(CC)CC)C.[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](Cl)(=[O:37])=[O:36])=[CH:31][CH:30]=1.O>ClCCl>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([S:35]([NH:1][CH:2]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH2:3][C:4]2[CH:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 18950756HCID 18950756, compound

Product 1

HCID 15232188HCID 15232188, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 0.11 g of methyl 4-[2-amino-2- (3-pyridyl)ethyl]phenylacetate in 10 ml of dichloromethane were added 0.07 ml of triethylamine (0.07 ml) and 0.11 g of p-chlorobenzenesulfonyl chloride, and stirred overnight at room temperature. After completion of reaction, water was added to the reaction mixture, which was then extracted with dichloromethane, followed by washing in saturated aqueous sodium chloride solution and dried over magnesium sulfate to obtain residue of 0.31 g. The residue was subjected to chromatography on a silica gel column, which was then eluted with chloroform-methanol (10:1 v/v) to produce 0.1 g of methyl 4-[2-(4-chlorobenzenesulfonamido)-2-(3-pyridyl)ethyl]phenylacetate. The spectrometric data thereof supports the structure of [28] as follows.

Workup

  1. additionwas added to the reaction mixture, which
  2. extractionwas then extracted with dichloromethane
  3. washby washing in saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customto obtain residue of 0.31 g
  6. washwas then eluted with chloroform-methanol (10:1 v/v)

Sources & evidence

ORD record
ord-a896c07a5a8849b2b0db89362360ce74
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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