Hydrochloric Acid → HCID 22666536, compound

HRID 1007898Notes

Reaction equation

HRID 1007898 reaction equation
CS(O[CH:6]([CH3:20])[CH2:7][O:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][C:14]2[S:15][CH:16]=[CH:17][C:13]=2[CH:12]=1)(=O)=O.[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22].O.Cl>CN(C)C=O.C(OCC)(=O)C>[S:15]1[CH:16]=[CH:17][C:13]2[CH:12]=[C:11]([CH2:10][CH2:9][O:8][CH2:7][CH:6]([N:23]([CH2:24][CH3:25])[CH2:21][CH3:22])[CH3:20])[CH:19]=[CH:18][C:14]1=2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8021DiethylamineHCID 22666396HCID 22666396, compound

Product 1

HCID 22666536HCID 22666536, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

In 10 mL of N,N-dimethylformamide is dissolved 1.00 g of 2-(2-benzo[b]thiophen-5-ylethoxy)-1-methylethyl methanesulfonate, to which is added 3.3 mL of diethylamine. The mixture thus obtained is stirred in an ampoule at 100° C. for 15 hours. After cooling, the reaction mixture is introduced into a mixture of water and ethyl acetate, pH is adjusted to 2.0 with 6 mol/L hydrochloric acid, and the aqueous layer is separated. Ethyl acetate is added to the aqueous layer, pH is adjusted to 9.5 with 5 mol/AL aqueous solution of sodium hydroxide, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride successively and dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is purified by column chromatography (eluent: chloroform:methanol=20:1 to 10:1). Thus, 0.63 g of N-[2-(2-benzo[b]thiophen-5-ylethoxy)-1-methylethyl]-N,N-diethylamine is obtained as an oily product.

Workup

  1. customThe mixture thus obtained
  2. temperatureAfter cooling
  3. customthe aqueous layer is separated
  4. additionEthyl acetate is added to the aqueous layer
  5. customthe organic layer is separated
  6. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride successively
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure
  9. customthe residue is purified by column chromatography (eluent: chloroform:methanol=20:1 to 10:1)

Sources & evidence

ORD record
ord-c00c7a71d0844b688f2299e74c7072dc
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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