Triethylamine → HCID 9933992, compound

HRID 2396556Notes

Reaction equation

HRID 2396556 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.[CH:45]([C:48]1[CH:54]=[CH:53][CH:52]=[C:51]([CH:55]([CH3:57])[CH3:56])[C:49]=1[NH2:50])([CH3:47])[CH3:46]>C1C=CC=CC=1>[CH3:56][CH:55]([C:51]1[CH:52]=[CH:53][CH:54]=[C:48]([CH:45]([CH3:47])[CH3:46])[C:49]=1[NH:50][C:43]([NH:40][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:20][C:6]=2[C:7]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:28])[CH3:57]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 32484DiisopropylanilineHCID 199401P,P-Diphenylphosphinic azideHCID 15410731HCID 15410731, compound

Product 1

HCID 9933992HCID 9933992, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 5-chloro-3-(2-methylphenyl) benzofuran-2-carboxylic acid (300 mg) in anhydrous benzene (10 ml) were added diphenyl phosphoryl azide (0.33 ml) and triethylamine (0.16 ml). The mixture was stirred for 15 minutes at room temperature, then heated under reflux for one hour. To the reaction mixture (containing 5-chloro-3-phenylbenzofuran-2-isocyanate) was added 2,6-diisopropyl aniline (0.3 ml), and the mixture was stirred with heating under reflux for 0.5 hour, then the solvent was distilled off. To the residue was added ethyl acetate, which was washed with water, dilute hydrochloric acid, water, an aqueous solution of sodium hydrogencarbonate and water, successively, followed by drying and distilling off the solvent to give the title compound as colorless crystals (217 mg).

Workup

  1. temperatureheated
  2. temperatureunder reflux for one hour
  3. stirringthe mixture was stirred
  4. temperaturewith heating
  5. temperatureunder reflux for 0.5 hour
  6. distillationthe solvent was distilled off
  7. additionTo the residue was added ethyl acetate, which
  8. washwas washed with water, dilute hydrochloric acid, water
  9. customby drying
  10. distillationdistilling off the solvent

Sources & evidence

ORD record
ord-468432d88bbe4b7f9a2af838436bbb26
Source dataset
uspto-grants-1996_02
Patent number
US05492929

Reaction notes

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