Triethylamine → HCID 15035164, compound

HRID 1656426Notes

Reaction equation

HRID 1656426 reaction equation
C(N(CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:25]([O:28][C:29]1[C:34]([CH:35]([CH3:37])[CH3:36])=[CH:33][C:32]([N:38]=[C:39]=[O:40])=[CH:31][C:30]=1[CH:41]([CH3:43])[CH3:42])(=[O:27])[CH3:26].[NH2:44][C:45]1[CH:46]=[N:47][C:48]2[C:53]([C:54]=1[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[Cl:61])=[CH:52][C:51]([CH3:62])=[CH:50][C:49]=2[CH3:63]>C1C=CC=CC=1.C(OCC)(=O)C>[C:25]([O:28][C:29]1[C:30]([CH:41]([CH3:43])[CH3:42])=[CH:31][C:32]([NH:38][C:39](=[O:40])[NH:44][C:45]2[CH:46]=[N:47][C:48]3[C:53]([C:54]=2[C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=2[Cl:61])=[CH:52][C:51]([CH3:62])=[CH:50][C:49]=3[CH3:63])=[CH:33][C:34]=1[CH:35]([CH3:37])[CH3:36])(=[O:27])[CH3:26]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 199401P,P-Diphenylphosphinic azideHCID 104465363-Amino-4-(2-chlorophenyl)-6,8-dimethylquinolineHCID 19788038Phenol, 4-isocyanato-2,6-bis(1-methylethyl)-, 1-acetate

Product 1

HCID 15035164HCID 15035164, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (0.15 ml) was dropwise added to a mixture of 4-acetoxy-3,5-didiisopropylbenzoic acid (238 mg), diphenylphosphoryl azide (300 mg) and benzene (10 ml) under stirring. The mixture was further stirred for 30 mins. at room temperature, and for 40 mins. under reflux to prepare a solution of 4-acetoxy-3,5-diisopropylphenylisocyanate. After cooling, to the solution were added a solution of 3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (255 mg) in benzene (255 mg) and then triethylamine (0.15 ml). The whole was stirred for 2 hrs. at room temperature, then for 3 hrs. under reflux, and thereto was added ethyl acetate. The organic layer was separated, washed with 2N-hydrochloric acid and water successively, and dried over anhydrous magnesium sulfate and then distilled to remove the solvent. The residue was recrystallized from a mixture of acetone and isopropyl ether to give 3-[3-(4-acetoxy-3,5-diisopropylphenyl)ureido]-4-(2-chlorophenyl)-6,8-dimethylquinoline as colorless needles. Yield 367 mg (74.9%). m.p. 248°-249° C.

Workup

  1. stirringThe mixture was further stirred for 30 mins
  2. temperatureunder reflux
  3. temperatureAfter cooling, to the solution
  4. stirringThe whole was stirred for 2 hrs
  5. waitat room temperature, then for 3 hrs
  6. temperatureunder reflux
  7. customThe organic layer was separated
  8. washwashed with 2N-hydrochloric acid and water successively
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationdistilled
  11. customto remove the solvent
  12. customThe residue was recrystallized from a mixture of acetone and isopropyl ether

Sources & evidence

ORD record
ord-9323831452be4f0289c2b3902e35b4a1
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

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