Triethylamine → (4-Bromo-3-methyl-phenyl)-(4H,10H-3a,5,9-triaza-benzo[f]azulen-9-yl)-methanone

HRID 2215161Notes

Reaction equation

HRID 2215161 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.[CH3:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[Br:25])[C:19](Cl)=[O:20].C(N(CC)CC)C>ClCCl>[Br:25][C:24]1[CH:23]=[CH:22][C:18]([C:19]([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:20])=[CH:17][C:16]=1[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70215344-Bromo-3-methylbenzoyl chlorideHCID 167520349,10-dihydro-4H-3a, 5,9-triaza-benzo[f]azulene

Product 1

HCID 21947848(4-Bromo-3-methyl-phenyl)-(4H,10H-3a,5,9-triaza-benzo[f]azulen-9-yl)-methanoneYield 111.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the 9,10-dihydro-4H-3a,5,9-triaza-benzo[f]azulene of Step D (1.0 g) in dichloromethane (10 mL) was added 3-methyl-4-bromobenzoyl chloride (1.39 g) and triethylamine (1.1 mL). After stirring for 2.5 hours, the reaction mixture was washed with water, dried over anhydrous magnesium sulfate, filtered and the solvent removed in vacuo to provide the title product as a tan crystalline solid (2.3 g), which was used without further purification.

Workup

  1. washthe reaction mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a98b94bdf34d4fb187230623ac568a47
Source dataset
uspto-grants-2006_09
Patent number
US07109193B2

Reaction notes

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