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

HRID 2184482Notes

Reaction equation

HRID 2184482 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 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-9931761b1dfd42d4b4e4061161243737
Source dataset
uspto-grants-2005_05
Patent number
US06900200B2

Reaction notes

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