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Sodium Hydroxide → N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-(2-hydroxy-1-methylethyl)-formamide

HRID 1007914
Notes
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Reaction equation

HRID 1007914 reaction equation
[CH:1]([O-])=[O:2].[Na+].C(Cl)(=O)C(C)(C)C.[S:12]1[CH:16]=[CH:15][C:14]2[CH:17]=[C:18]([CH2:21][CH2:22][O:23][CH2:24][CH2:25][NH:26][CH:27]([CH3:30])[CH2:28][OH:29])[CH:19]=[CH:20][C:13]1=2.[OH-].[Na+]>CC(C)=O.C(OCC)(=O)C.O>[S:12]1[CH:16]=[CH:15][C:14]2[CH:17]=[C:18]([CH2:21][CH2:22][O:23][CH2:24][CH2:25][N:26]([CH:27]([CH3:30])[CH2:28][OH:29])[CH:1]=[O:2])[CH:19]=[CH:20][C:13]1=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 62493Pivaloyl chlorideHCID 2723810Sodium FormateHCID 226664502-{[2-(2-Benzo[b]thiophen-5-ylethoxy)ethyl]amino}-1-propanol

Product 1

HCID 22666440N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-(2-hydroxy-1-methylethyl)-formamideYield 83.6%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolvent2×
HCID 962WaterSolvent
HCID 8857Ethyl AcetateSolvent

Procedure

In 2.4 mL of acetone is suspended 0.38 g of sodium formate, to which is added 0.37 mL of pivaloyl chloride. The mixture is stirred at ambient temperature for 2 hours. Then, at an ice-cooled temperature, 4 mL of a solution of 0.50 g of 2-{[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-amino}-1-propanol in acetone is added, and the resulting mixture is stirred at ambient temperature for 2 hours. Water and ethyl acetate are added to the reaction mixture, pH is adjusted to 8.5 with 2 mol/L aqueous solution of sodium hydroxide, and the organic layer is separated. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent: chloroform). Thus, 0.46 g of N-[2-(2-benzo[b]thiophen-5-ylethoxy)ethyl]-N-(2-hydroxy-1-methylethyl)-formamide (is obtained as an oily product.

Workup

  1. additionis added
  2. stirringthe resulting mixture is stirred at ambient temperature for 2 hours
  3. customthe organic layer is separated
  4. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent is distilled off under reduced pressure
  7. customthe residue is purified by column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-f4c9fdec0f42441bb8087eee456799fe
Source dataset
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06797726B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes