Hydrochloric Acid → HCID 14719514, compound

HRID 465918Notes

Reaction equation

HRID 465918 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=O.[C:13](Cl)(=[O:17])[O:14][CH2:15][CH3:16].[NH2:19][CH2:20][CH2:21][S:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].Cl>C(Cl)Cl.C(N(CC)CC)C>[CH2:15]([O:14][C:13]([O:12][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][C:6]=1[C:7]([NH:19][CH2:20][CH2:21][S:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:9])=[O:17])[CH3:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 752314-Methoxysalicylic AcidHCID 13628032HCID 13628032, compound

Product 1

HCID 14719514HCID 14719514, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
-15 °C

Procedure

In the meantime, 3.36 g of 4-methoxysalicylic acid was dispersed in 30 ml of methylene chloride under argon atmosphere, and the dispersion was cooled to -15° C. To the dispersion were added 4.47 g of triethylamine and 4.58 g of ethyl chlorocarbonate, and the mixture was agitated for 1.5 hours. To the mixture was added the 2-aminoethyl-n-octylsulfide which had been dissolved in 10 ml of methylene chloride, and the mixture was agitated at -15° C. for 2 hours. The reaction mixture was poured into 1N aqueous hydrochloric acid, and the mixture was extracted with methylene chloride. The organic layer was washed with saturated aqueous solution of sodium bicarbonate, and dried over anhydrous sodium sulfate. The solvent was distilled off in evacuated atomosphere, and the residue was subjected to column chromatography using silica gel. There was obtained 6.37 g of 2-(2'-ethoxycarbonyloxy-4'-methoxybenzoylamino)ethyl-n-octylsulfide, which was dissolved in 100 ml of methanol. To the solution was added 23 ml of 1N aqueous solution of sodium hydroxide, and the mixture was agitated for 35 minutes. The solvent was distilled off in evacuated atomosphere, and the residue was subjected to column chromatography using silica gel. There was obtained 3.55 g of 2-(2'-hydroxy-4'-methoxybenzoylamino)ethyl-n-octylsulfide.

Workup

  1. stirringthe mixture was agitated at -15° C. for 2 hours
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off in evacuated atomosphere

Sources & evidence

ORD record
ord-ae6698b32aed4d558c8aa599d448a7e2
Source dataset
uspto-grants-1992_10
Patent number
US05155106

Reaction notes

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