Iodoethane → HCID 15027726, compound

HRID 373154Notes

Reaction equation

HRID 373154 reaction equation
[CH2:1](I)[CH3:2].[OH:4][CH:5]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:21][CH:20]=1)[CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[OH:4][CH:5]([C:19]1[CH:20]=[CH:21][C:22]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:23][CH:24]=1)[CH2:6][CH2:7][CH2:8][N:9]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=1)[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 15027724HCID 15027724, compound

Product 1

HCID 15027726HCID 15027726, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

0.24 ml (3.04 mmol) of ethyl iodide was added to a suspension of 1.0 g (2.77 mmol) of N-[4-[1-hydroxy-4-[2-(6-methyl-2-pyridyl)ethylamino]butyl]phenyl]methanesulfonamide prepared in Example 3-(4) and 0.70 g (8.31 mmol) of sodium hydrogencarbonate in 15 ml of dimethylformamide. The mixture was stirred at 50° C. for 2 h and then filtered. The filtrate was concentrated to give a residue, which was purified by silica gel column chromatography (chloroform/methanol/aqueous ammonia=97:3:0.3). 0.96 g (yield: 89%) of the intended compound was obtained in the form of a colorless oil.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. customto give a residue, which
  4. customwas purified by silica gel column chromatography (chloroform/methanol/aqueous ammonia=97:3:0.3)

Sources & evidence

ORD record
ord-5f25d529d8ab442cbf59e997508ffe5c
Source dataset
uspto-grants-1992_11
Patent number
US05162347

Reaction notes

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