2-Bromopropane → HCID 54412198, compound

HRID 280048Notes

Reaction equation

HRID 280048 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:33])[CH2:14][CH2:15][CH2:16][S:17]([NH:20][C:21]2[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[C:23]([O:31][CH3:32])[CH:22]=2)(=[O:19])=[O:18])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].Br[CH:37]([CH3:39])[CH3:38]>CN(C)C=O.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][N:13]([CH3:33])[CH2:14][CH2:15][CH2:16][S:17]([N:20]([CH:37]([CH3:39])[CH3:38])[C:21]2[CH:22]=[C:23]([O:31][CH3:32])[C:24]([O:29][CH3:30])=[C:25]([O:27][CH3:28])[CH:26]=2)(=[O:19])=[O:18])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 13645638HCID 13645638, compound

Product 1

HCID 54412198HCID 54412198, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

3-[[2-(3,4-Dimethoxyphenyl)ethyl]methylamino]-N-(3,4,5-trimethoxyphenyl)-1-propanesulfonamide (6.7 g, 0.0139 mol) in dry dimethylformamide (100 mL) was treated with sodium hydride, 60% in mineral oil, (0.555 g, 0.0139 mol) and the reaction stirred 1 hour at which point 2-bromopropane (1.71 g, 0.0139 mol) was added and the solution warmed overnight. The reaction was then stripped, dissolved in methylene chloride, filtered and evaporated to a gum. Preparative high pressure chromatography provided the title compound (3.40 g).

Workup

  1. additionwas added
  2. temperaturethe solution warmed overnight
  3. filtrationfiltered
  4. customevaporated to a gum

Sources & evidence

ORD record
ord-c91e121e5f224194bd9d7cbda342d66b
Source dataset
uspto-grants-1986_05
Patent number
US04587360

Reaction notes

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