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

HRID 1830103Notes

Reaction equation

HRID 1830103 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-a5a41ffbd767449184ba35654285c42a
Source dataset
uspto-grants-2006_06
Patent number
US07064120B2

Reaction notes

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