Triethylamine → HCID 54376430, compound

HRID 1084826Notes

Reaction equation

HRID 1084826 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])=[O:9].C(N(CC)CC)C.Br[CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:30](=[O:31])[O:29]1>CC(C)=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[CH:7][C:8]([NH:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13]([O:15][CH:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:30](=[O:31])[O:29]1)=[O:14])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 962181(3H)-Isobenzofuranone, 3-bromo-HCID 3063368HCID 3063368, compound

Product 1

HCID 54376430HCID 54376430, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 2-[3-(2-thienyl)acrylamido]benzoic acid (273 mg, 1 mmol) and triethylamine (0.14 ml, 1 mmol) in dry acetone (10 ml) was stirred at room temperature for 30 minutes. A solution of 3-bromophtalide (213 mg, 1 mmol) in acetone (2 ml) was added under ice cooling, and the mixture was stirred at room temperature for 23 hours. The reaction mixture was filtered by suction, and the solvent was removed from the filtrate. The residue was dissolved in chloroform, washed with saturated aqueous sodium hydrogen carbonate, then with saturated aqueous sodium chloride, and dried over magnesium sulfate. The solvent was removed and the residue was purified by silica gel column chromatography (developing solvent: benzene:ether=49:1). The pale yellow second eluate was collected. After removing the solvent, the resulting oily product was crystallized with isopropyl ether to give the desired compound (159 mg, yield, 39%). m.p., 194°-195° C. (white crystals, recrystallized from benzene-n-hexane)

Workup

  1. stirringthe mixture was stirred at room temperature for 23 hours
  2. filtrationThe reaction mixture was filtered by suction
  3. customthe solvent was removed from the filtrate
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with saturated aqueous sodium hydrogen carbonate
  6. dry with materialwith saturated aqueous sodium chloride, and dried over magnesium sulfate
  7. customThe solvent was removed
  8. customthe residue was purified by silica gel column chromatography (developing solvent: benzene:ether=49:1)
  9. customThe pale yellow second eluate was collected
  10. customAfter removing the solvent
  11. customthe resulting oily product was crystallized with isopropyl ether

Sources & evidence

ORD record
ord-c178c6e047f24a64943c5a7b641a3ed8
Source dataset
uspto-grants-1991_04
Patent number
US05006548

Reaction notes

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