Hydrochloric Acid → HCID 15023278, compound

HRID 129339Notes

Reaction equation

HRID 129339 reaction equation
[CH2:1]([C:14]1[NH:18][CH:17]=[C:16]([C:19]([OH:21])=[O:20])[CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(Cl)(=O)OCC.C(N(CC)CC)C.[Br:35][CH2:36][CH2:37]O.Cl>O1CCCC1>[CH2:1]([C:14]1[NH:18][CH:17]=[C:16]([C:19]([O:21][CH2:37][CH2:36][Br:35])=[O:20])[CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 108982-Bromoethanol2×HCID 10928Ethyl chloroformateHCID 15023289HCID 15023289, compound

Product 1

HCID 15023278HCID 15023278, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (20 ml) of 1.47 g (5.0 mmol) of 5-tridecylpyrrole-3-carboxylic acid in tetrahydrofuran were added 0.60 g (5.53 mmol) of ethyl chlorocarbonate and 0.60 g (5.94 mmol) of triethylamine, and the whole was stirred at room temperature for 10 minutes. After adding 1.88 g (15 mmol) of 2-bromoethanol, the mixture was heated under reflux for 1.5 hours. After further addition of 0.94 (7.5 mmol) of 2-bromoethanol, the mixture was heated under reflux for 9 hours. The resulting mixture was cooled, acidified with a diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate. A removal of the solvent under reduced pressure afforded an oily product, which was purified by subjecting it to column chromatography over silica gel (eluent: ethyl acetate/hexane=1/10) to obtain 1.05 g (53% yield) of 2-bromoethyl 5-tridecylpyrrole-3-carboxylate, m.p. 67°-69.5° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 9 hours
  5. temperatureThe resulting mixture was cooled
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialdried over magnesium sulfate
  9. customA removal of the solvent under reduced pressure
  10. customafforded an oily product, which
  11. customwas purified

Sources & evidence

ORD record
ord-49feba7d9d234d3387c4efa1c60c3970
Source dataset
uspto-grants-1995_11
Patent number
USRE035096

Reaction notes

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