Triethylamine → HCID 18688806, compound

HRID 1871803Notes

Reaction equation

HRID 1871803 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]2[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]=2[O:10][C:9]=1C(O)=O.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:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]2[CH:13]=[C:14]([CH3:17])[CH:15]=[CH:16][C:11]=2[O:10][C:9]=1[NH:40][C:43]([NH:49][C:48]1[C:50]([CH2:54][CH3:55])=[CH:51][CH:52]=[CH:53][C:47]=1[CH2:45][CH3:46])=[O:28]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 113692,6-DiethylanilineHCID 199401P,P-Diphenylphosphinic azideHCID 186887823-(2-Chlorophenyl)-5-methylbenzofuran-2-carboxylic acid

Product 1

HCID 18688806HCID 18688806, compoundYield 68.7%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 430 mg of 3-(2-chlorophenyl)-5-methylbenzofuran-2-carboxylic acid and 0.39 cc of diphenylphosphoryl azide in 6 cc of benzene was added dropwise 0.22 cc of triethylamine at room temperature. The resulting mixture was stirred at room temperature for 35 minutes and then heated under reflux for 15 minutes. After cooling, 0.30 cc of 2,6-diethylaniline was added, followed by refluxing for 2 hours. After cooling, water was added to the reaction mixture and 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 446 mg of compound 21.

Workup

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

Sources & evidence

ORD record
ord-6ad44e28bac84217961e061562b2b80f
Source dataset
uspto-grants-2000_08
Patent number
USRE036832

Reaction notes

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