Dimethylformamide → HCID 21990156, compound

HRID 7458Notes

Reaction equation

HRID 7458 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

In 7.0 mL of methylene chloride was dissolved 1.40 g of 3-[2-(1-benzothiophen-4-yl)ethoxy]-1-propanol, followed by adding thereto 1.10 mL of thionyl chloride and 0.05 mL of N,N-dimethylformamide, and the resulting mixture was heated under reflux for 5 hours. Then, the solvent was distilled off under reduced pressure. The residue was purified by a column chromatography (eluent; hexane:ethyl acetate=20:1) to obtain 1.43 g of 4-[2-(3-chloropropoxy)ethyl]-1-benzothiophene as a yellow oil.

Workup

  1. additionby adding
  2. temperatureunder reflux for 5 hours
  3. distillationThen, the solvent was distilled off under reduced pressure
  4. customThe residue was purified by a column chromatography (eluent; hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-b1be6064558b4bf8b5568e3fb5a9afe1
Source dataset
uspto-grants-2006_08
Patent number
US07087594B2

Reaction notes

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