4-Chlorobenzenesulfonyl chloride → Diethyl [4-(p-chlorophenylsulfonamido)butyl][3-(3-pyridyl)propyl]-malonate

HRID 465520Notes

Reaction equation

HRID 465520 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(N(CC)CC)C.[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([S:40](Cl)(=[O:42])=[O:41])=[CH:36][CH:35]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([S:40]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([CH2:17][CH2:18][CH2:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:42])=[O:41])=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 10383244Diethyl [4-aminobutyl][3-(3-pyridyl)propyl]-malonate

Product 1

HCID 14986635Diethyl [4-(p-chlorophenylsulfonamido)butyl][3-(3-pyridyl)propyl]-malonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 15.0 g (42.8 mmol) of diethyl [4-aminobutyl][3-(3-pyridyl)propyl]-malonate in 115 ml methylene chloride is cooled to 0° and 0.1 g 4-dimethylaminopyridine is added followed by 8.4 ml (60 mmol) triethylamine and 10.12 g (46.5 mmol) p-chlorophenylsulfonyl chloride. The solution is stirred at room temperature for 48 h and then washed with saturated aqueous sodium bicarbonate solution. The organic phase is dried (MgSO4), filtered and evaporated to give diethyl [4-(p-chlorophenylsulfonamido)butyl][3-(3-pyridyl)propyl]-malonate as an oil.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase is dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-7a6f4a9ec7ca4e678e4c4ce29c151c8d
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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