Dimethylformamide → HCID 21990156, compound

HRID 597823Notes

Reaction equation

HRID 597823 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15]O)[C:4]=2[CH:3]=[CH:2]1.S(Cl)([Cl:19])=O.CN(C)C=O>C(Cl)Cl>[Cl:19][CH2:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][C:9]1[C:4]2[CH:3]=[CH:2][S:1][C:5]=2[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 219901773-(2-(1-Benzothiophene-4-yl)ethoxy)-1-propanol

Product 1

HCID 21990156HCID 21990156, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.40 g of 3-(2-(1-benzothiophene-4-yl)ethoxy)-1-propanol was dissolved in 7.0 ml of methylene chloride. Thereafter, 1.10 ml of thionyl chloride and 0.05 ml of N,N-dimethylformamide were added to the obtained solution, and the obtained mixture was then heated to reflux for 5 hours. Subsequently, the solvent was distilled away under a reduced pressure. The residue was purified by column chromatography (eluent; hexane:ethyl acetate=20:1), so as to obtain 1.43 g of a yellow oil product, 4-(2-(3-chloropropoxy)ethyl)-1-benzothiophene.

Workup

  1. temperaturethe obtained mixture was then heated
  2. temperatureto reflux for 5 hours
  3. distillationSubsequently, the solvent was distilled away under a reduced pressure
  4. customThe residue was purified by column chromatography (eluent; hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-a4567b16afe646408f7190ec9fefe142
Source dataset
uspto-grants-2011_03
Patent number
US07897594B2

Reaction notes

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