Triethylamine → HCID 18688812, compound

HRID 1871805Notes

Reaction equation

HRID 1871805 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](C(O)=O)=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])[C:6]=2[CH:20]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.C([N:40]([CH2:43]C)CC)C.[CH2:45]([C:47]1[CH:53]=[CH:52][CH:51]=[C:50]([CH2:54][CH3:55])[C:48]=1[NH2:49])[CH3:46]>C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([NH:40][C:43]([NH:49][C:48]3[C:50]([CH2:54][CH3:55])=[CH:51][CH:52]=[CH:53][C:47]=3[CH2:45][CH3:46])=[O:28])=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])[C:6]=2[CH:20]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 113692,6-DiethylanilineHCID 199401P,P-Diphenylphosphinic azideHCID 15410731HCID 15410731, compound

Product 1

HCID 18688812HCID 18688812, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To stirred a mixture of 573 mg of 5-chloro-3(2-methylphenyl)benzofuran-2-carboxylic acid and 0.47 cc of diphenylphosphoryl azide in 6 cc of benzene was added dropwise 0.30 cc of triethylamine at room temperature. The resulting mixture was stirred at room temperature for 30 minutes and then heated under reflux for 15 minutes. After cooling, 0.36 cc of 2,6-diethylaniline was added, followed by refluxing for 2 hours. After cooling, water was added to the reaction mixture and was extracted with chloroform. The extract was dried over magnesium sulfate, and distilled to remove the solvent. The crude product thus obtained was purified by a silica gel column chromatography (eluent: chloroform) to obtain 219 mg of compound 60.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 30 minutes
  2. temperatureheated
  3. temperatureunder reflux for 15 minutes
  4. temperatureAfter cooling
  5. temperatureby refluxing for 2 hours
  6. temperatureAfter cooling
  7. extractionwas extracted with chloroform
  8. dry with materialThe extract was dried over magnesium sulfate
  9. distillationdistilled
  10. customto remove the solvent
  11. customThe crude product thus obtained
  12. customwas purified by a silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-aa177d122c384257adac26e1bdeff13a
Source dataset
uspto-grants-2000_08
Patent number
USRE036832

Reaction notes

Loading…