Triethylamine → HCID 15410726, compound

HRID 583225Notes

Reaction equation

HRID 583225 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10]C(O)=O)=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH3:20])[C:6]=2[CH:21]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.C([N:41]([CH2:44]C)CC)C.[F:46][C:47]1[CH:53]=[C:52]([F:54])[CH:51]=[CH:50][C:48]=1[NH2:49]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][NH:41][C:44]([NH:49][C:48]3[CH:50]=[CH:51][C:52]([F:54])=[CH:53][C:47]=3[F:46])=[O:29])=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH3:20])[C:6]=2[CH:21]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 97092,4-DifluoroanilineHCID 199401P,P-Diphenylphosphinic azideHCID 15813579HCID 15813579, compound

Product 1

HCID 15410726HCID 15410726, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 5-chloro-3-(2-methylphenyl)benzofuran-2-acetic 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 this reaction mixture {containing 2-[5-chloro-3-(2-methylphenyl)benzofuryl]methyl isocyanate} was added 2,4-difluoroaniline (0.30 ml), and the mixture was stirred with heating under reflux for 0.5 hour. 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. The residue was purified by means of a silica gel (30 g) column chromatography (hexane-ethyl acetate=3:1) to afford the title compound as colorless crystals (63 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
  11. customThe residue was purified by means of a silica gel (30 g) column chromatography (hexane-ethyl acetate=3:1)

Sources & evidence

ORD record
ord-65b4f9ddf7db417a8f30531ace1c1f2a
Source dataset
uspto-grants-1999_07
Patent number
US05929107

Reaction notes

Loading…