Hydrochloric Acid → HCID 68796619, compound

HRID 1007905Notes

Reaction equation

HRID 1007905 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:12][CH2:13][O:14][CH2:15][C:16]([OH:18])=O)=[CH:5][C:6]2[CH:10]=[CH:9][S:8][C:7]=2[CH:11]=1.N1C=CN=C1.S(Cl)(Cl)=O.[CH3:28][NH:29][CH2:30][CH2:31][OH:32].Cl>C(Cl)Cl.O.C(N(CC)CC)C>[OH:32][CH2:31][CH2:30][N:29]([CH3:28])[C:16](=[O:18])[CH2:15][O:14][CH2:13][CH2:12][C:4]1[C:3]([O:2][CH3:1])=[CH:11][C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 80162-(Methylamino)ethanolHCID 24386Thionyl ChlorideHCID 22666344HCID 22666344, compound

Product 1

HCID 68796619HCID 68796619, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent2×

Conditions

Temperature
5 °C

Procedure

In 8 mL of methylene chloride is dissolved 0.80 g of 2-[2-(6-methoxybenzo[b]thiophen-5-yl)ethoxy]-acetic acid, to which are added 1.38 mL of triethylamine and 0.22 g of imidazole. The mixture is cooled to 5° C., to which is dropwise added a mixture of 0.24 mL of thionyl chloride and 8 mL of methylene chloride. The resulting mixture is stirred at the same temperature as above for one hour. The reaction mixture is cooled to −60° C., 0.47 mL of triethylamine and 0.31 mL of 2-(methylamino)-ethanol are added thereto, and the resulting mixture is stirred at the same temperature as above for one hour and the at ambient temperature for 1.5 hours. Water is added to the reaction mixture, pH is adjusted to 1.0 with 6 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, 0.93 g of N1-(2-hydroxyethyl)-N1-methyl-2-[2-(6-methoxybenzo[b]thiophen-5-yl)ethoxy]-acetamide is obtained as an oily product.

Workup

  1. additionis dropwise added
  2. temperatureThe reaction mixture is cooled to −60° C.
  3. stirringthe resulting mixture is stirred at the same temperature as above for one hour
  4. waitthe at ambient temperature for 1.5 hours
  5. customthe organic layer is separated
  6. washThe organic layer is washed with saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-c6b5f2a8c602417ea1905772ffda67a6
Source dataset
uspto-grants-2004_09
Patent number
US06797726B1

Reaction notes

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