Potassium Carbonate → 1-{3-Bromo-2-[2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one

HRID 628518Notes

Reaction equation

HRID 628518 reaction equation
Br[CH2:2][C:3]1[C:8]([Br:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[C:14](=[O:15])[N:13]([CH3:16])[N:12]=[N:11]1.[CH3:17][C:18]1[CH:23]=[C:22]([N:24]2[C:28]([CH3:29])=[C:27]([CH3:30])[C:26]([CH3:31])=[N:25]2)[CH:21]=[CH:20][C:19]=1[OH:32].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:9][C:8]1[C:3]([CH2:2][O:32][C:19]2[CH:20]=[CH:21][C:22]([N:24]3[C:28]([CH3:29])=[C:27]([CH3:30])[C:26]([CH3:31])=[N:25]3)=[CH:23][C:18]=2[CH3:17])=[C:4]([N:10]2[C:14](=[O:15])[N:13]([CH3:16])[N:12]=[N:11]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 898756621-(2-Bromomethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-oneHCID 118236550Methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenol

Product 1

HCID 1182365091-{3-Bromo-2-[2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-oneYield 86.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(2-bromomethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 11) 3.1 g, 2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenol (described in Reference Preparation example 20) 1.6 g, potassium carbonate 1.3 g and acetonitrile 70 ml was stirred with heating under reflux for six hours, and the reaction mixture was then filtered and was concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-{ 3-bromo-2-[2-methyl-4-(3,4,5-trimethyl-pyrazol-1-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one 3.1 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for six hours
  3. filtrationthe reaction mixture was then filtered
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-28959d94acf241d6b9a41cf38fe91f95
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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