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Potassium Carbonate → 1-{4-[4-bromo-1-(2-methylpropyl)-1H-benzotriazol-5-yl]benzyl}-3-methylimidazolidine-2,4-dione

HRID 2281059
Notes
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Reaction equation

HRID 2281059 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Cl)=[CH:17][CH:16]=1.[CH3:23][N:24]1[C:28](=[O:29])[CH2:27][NH:26][C:25]1=[O:30].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.ClCCl>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:26]2[CH2:27][C:28](=[O:29])[N:24]([CH3:23])[C:25]2=[O:30])=[CH:17][CH:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1388512,4-Imidazolidinedione, 3-methyl-HCID 867119834-bromo-5-[4-(chloromethyl)phenyl]-1-(2-methylpropyl)-1H-benzotriazole

Product 1

HCID 709783811-{4-[4-bromo-1-(2-methylpropyl)-1H-benzotriazol-5-yl]benzyl}-3-methylimidazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 6342
Acetonitrile
Solvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

4-Bromo-5-[4-(chloromethyl)phenyl]-1-(2-methylpropyl)-1H-benzotriazole (170 mg, 0.449 mmol), 3-methylimidazolidine-2,4-dione (102 mg, 0.898 mmol) and potassium carbonate (186 mg, 1.347 mmol) were combined in acetonitrile (3 ml) and heated at 50° C. for 16 hours. The mixture was cooled to ambient temperature, diluted with dichloromethane and filtered. The filtrate was washed with aqueous saturated ammonium chloride and brine. The organic extract was dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography (acetone/dichloromethane gradient), providing the titled compound as white solid: 1H NMR (500 MHz, d6-DMSO): 1H NMR δ 8.00 (d, J=8.5 Hz, 1H), 7.55 (d, J=8.5 Hz, 1H), 7.48 (d, J=7.9 Hz, 2H), 7.42 (d, J=7.9 Hz, 2H), 4.60-4.57 (m, 4H), 3.97 (s, 2H), 2.90 (s, 3H), 2.34-2.27 (m, 1H), 0.93-0.88 (m, 6H) ppm. LRMS m/z (M+H) 455.9 and 457.9 found, 456.1 and 458.1 required.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with aqueous saturated ammonium chloride and brine
  4. extractionThe organic extract
  5. dry with materialwas dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via silica gel chromatography (acetone/dichloromethane gradient)

Sources & evidence

ORD record
ord-8defa58226784688a602e8bb72407fc0
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09139576B2

Reaction notes

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