Hydrochloric Acid → HCID 22666443, compound

HRID 1007883Notes

Reaction equation

HRID 1007883 reaction equation
[F:1][C:2]1[C:3]([CH2:11][CH2:12][O:13][CH2:14][C:15]([OH:17])=O)=[CH:4][C:5]2[CH:9]=[CH:8][S:7][C:6]=2[CH:10]=1.[C:18](Cl)(=O)[C:19](Cl)=O.C[N:25]([CH3:28])C=O.Cl.[CH2:30](Cl)Cl>O>[CH2:28]([N:25]([CH2:18][CH3:19])[C:15](=[O:17])[CH2:14][O:13][CH2:12][CH2:11][C:3]1[C:2]([F:1])=[CH:10][C:6]2[S:7][CH:8]=[CH:9][C:5]=2[CH:4]=1)[CH3:30]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 22666327HCID 22666327, compound

Product 1

HCID 22666443HCID 22666443, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

In 10 mL of methylene chloride is dissolved 1.00 g of 2-[2-(6-fluorobenzo[b]thiophen-5-yl)ethoxy]-acetic acid. The solution is cooled to 5° C., 0.55 g of oxalyl chloride and 0.1 mL of N,N-dimethylformamide are added thereto, and the resulting mixture is stirred at ambient temperature for 2 hours. Water is added to the reaction mixture, pH is adjusted to 1.0 with 2 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. Thus, 1.24 g of N,N-diethyl-2-[2-(6-fluorobenzo[b]thiophen-5-yl)ethoxy]acetamide is obtained as an oily product.

Workup

  1. customthe organic layer is separated
  2. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-0fb14e288a90448aab10349b1704a871
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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