Triethylamine → 1,1'-Biphenyl-4-yl-(4H, 10H-3a,5,9-triaza-benzo[f]azulen-9-yl)-methanone

HRID 1070432Notes

Reaction equation

HRID 1070432 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[C:10]=1[CH2:9][NH:8][C:7]1[CH:11]=[CH:12][CH:13]=[N:14][C:6]=1[CH2:5]2.[C:15]1([C:21]2[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[C:21]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:22]=[CH:23][C:24]([C:25]([N:8]2[CH2:9][C:10]3[N:4]([CH:3]=[CH:2][CH:1]=3)[CH2:5][C:6]3[N:14]=[CH:13][CH:12]=[CH:11][C:7]2=3)=[O:26])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 167520349,10-dihydro-4H-3a, 5,9-triaza-benzo[f]azulene

Product 1

HCID 101557261,1'-Biphenyl-4-yl-(4H, 10H-3a,5,9-triaza-benzo[f]azulen-9-yl)-methanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred mixture of 9,10-dihydro-4H-3a, 5, 9-triaza-benzo[f]azulene of Step D (0.54 mmol), 4-phenylbenzoylchloride (1.08 mmol) and triethylamine (1.08 mmol) in toluene was refluxed under nitrogen for 72 hours. The reaction was cooled and the solvent removed in vacuo. Chromatography of the residue over silica gel Merck-60 with a solvent gradient from 5 to 20% ethyl acetate in hexane provided the title compound as a tan solid.

Workup

  1. temperaturewas refluxed under nitrogen for 72 hours
  2. temperatureThe reaction was cooled
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-9795b4581f474df79373fefc34721bc0
Source dataset
uspto-grants-2005_06
Patent number
US06903091B2

Reaction notes

Loading…