Triethylamine → HCID 19096904, compound

HRID 893194Notes

Reaction equation

HRID 893194 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.C(N(CC)CC)C.Cl[C:18]([C:20]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:23][CH2:22][CH2:21]1)=[O:19]>O1CCCC1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18]([C:20]2([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:23][CH2:22][CH2:21]2)=[O:19])=[C:4]([CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 114234-Bromo-2-methylanilineHCID 19096810Ethyl 1-(chlorocarbonyl)cyclobutane-1-carboxylate

Product 1

HCID 19096904HCID 19096904, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a nitrogen-purged reaction flask was charged 2.74 grams (0.01 mole) of 4-bromo-2-methylaniline and 1.49 grams (0.0) mole) of triethylamine dissolved in 200 milliliters of tetrahydrofuran. With vigorous stirring, 2.80 grams (0.01 mole) of ethyl 1-chlorocarbonylcyclobutanecarboxylate prepared in Example XIX were added and the resulting mixture stirred at ambient temperature for 6 hours. A precipitate of triethylamine hydrochloride was removed by filtration. The filtrate was vacuum stripped and the residue taken up in methylene chloride. This solution was washed successively with 2N HCl (2×75 milliliters) and water, and then dried over magnesium sulfate. Rotary evaporation gave a crude product which was flash chromatographed on silica using 7:3 hexane-ethyl acetate to give 3.68 grams (0.01 mole) of ethyl 1-(4-bromo-2-methylphenylaminocarbonyl)cyclobutanecarboxylate as a white solid. A small sample which was recrystallized from hexane had a melting point of 61° C.-64° C.

Workup

  1. customInto a nitrogen-purged
  2. customreaction flask
  3. customA precipitate of triethylamine hydrochloride was removed by filtration
  4. washThis solution was washed successively with 2N HCl (2×75 milliliters) and water
  5. dry with materialdried over magnesium sulfate
  6. customRotary evaporation
  7. customgave a crude product which
  8. customchromatographed on silica using 7:3 hexane-ethyl acetate

Sources & evidence

ORD record
ord-a1cd14a53edd4a179a81bfae2b64eca3
Source dataset
uspto-grants-1992_06
Patent number
US05123951

Reaction notes

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