Triethylamine → HCID 14719516, compound

HRID 465919Notes

Reaction equation

HRID 465919 reaction equation
[OH:1][C:2]1[C:10]([CH2:11][CH2:12][CH3:13])=[C:9]([O:14][CH3:15])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.[C:23](Cl)(=[O:27])[O:24][CH2:25][CH3:26].[NH2:29][CH2:30][CH2:31][S:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40]>C(Cl)Cl>[CH2:25]([O:24][C:23]([O:1][C:2]1[C:10]([CH2:11][CH2:12][CH3:13])=[C:9]([O:14][CH3:15])[CH:8]=[CH:7][C:3]=1[C:4]([NH:29][CH2:30][CH2:31][S:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])=[O:6])=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 13628032HCID 13628032, compoundHCID 14719507HCID 14719507, compound

Product 1

HCID 14719516HCID 14719516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

In the meantime, 6.00 g of 2-hydroxy-3-n-propyl-4-methoxy-benzoic acid was dispersed in 120 ml of methylene chloride, and the dispersion was cooled to -10° C. To the dispersion were added 9.93 ml of triethylamine and 5.45 ml of ethyl chlorocarbonate, and the mixture was agitated for 30 minutes. To the mixture was added the mixture of 2-aminoethyl-n-octylsulfide and hydrazide which had been dispersed in methylene chloride. The mixture was agitated at -10° C. to 0° C. for 3 hours. The reaction mixture was filtered, and the precipitate was washed with methylene chloride. The filtrate and the wash solution was combined, washed with water and then with saturated aqueous solution of sodium chloride, 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 6.28 g of 2-(2'-ethoxycarbonyloxy-3'-n-propyl-4'-methoxybenzoylamino)ethyl-n-octylsulfide.

Workup

  1. additionTo the mixture was added
  2. stirringThe mixture was agitated at -10° C. to 0° C. for 3 hours
  3. filtrationThe reaction mixture was filtered
  4. washthe precipitate was washed with methylene chloride
  5. washwashed with water
  6. dry with materialwith saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off in evacuated atomosphere

Sources & evidence

ORD record
ord-226a15d517f04269a8e8c588f1978edc
Source dataset
uspto-grants-1992_10
Patent number
US05155106

Reaction notes

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