Water → HCID 18950689, compound

HRID 1492553Notes

Reaction equation

HRID 1492553 reaction equation
[NH2:1][CH:2]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:3][CH2:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=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][CH2:4][C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=2)(=[O:37])=[O:36])=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 18950694HCID 18950694, compound

Product 1

HCID 18950689HCID 18950689, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 10 ml of the solution of 0.35 g of methyl 4-[3-amino-3-(3-pyridyl)propyl]benzoate in dichloromethane were added 0.22 ml of triethylamine and 0.33 g of p-chlorobenzene sulfonylchloride, and stirred at room temperature overnight. After completion of the reaction, the reaction mixture was poured into water, which was then extracted with dichloromethane, washed in saturated aqueous sodium chloride, and dried over magnesium sulfate. The residue was subjected to chromatography on a silica gel column, to obtain 0.34 g of methyl 4-[3-(4-chlorobenzenesulfonamido)-3-(3-pyridyl)propyl]benzoate. The spectrometric data supports the structure of [36] as follows.

Workup

  1. customAfter completion of the reaction
  2. extractionwas then extracted with dichloromethane
  3. washwashed in saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-cfab2476c3834deba4b5587b8f4a7924
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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