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

HRID 2375164Notes

Reaction equation

HRID 2375164 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-c116e5ab22584d03a61d8a8e950afca8
Source dataset
uspto-grants-2008_12
Patent number
US07465722B2

Reaction notes

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