Potassium Carbonate → 1-{3-methylthio-2-[2-methyl-4-(5-chloro-1,4-dimethyl-1H-pyrazol-3-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one

HRID 628482Notes

Reaction equation

HRID 628482 reaction equation
Br[CH2:2][C:3]1[C:8]([S:9][CH3:10])=[CH:7][CH:6]=[CH:5][C:4]=1[N:11]1[C:15](=[O:16])[N:14]([CH3:17])[N:13]=[N:12]1.[Cl:18][C:19]1[N:23]([CH3:24])[N:22]=[C:21]([C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[C:27]([CH3:32])[CH:26]=2)[C:20]=1[CH3:33].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:10][S:9][C:8]1[C:3]([CH2:2][O:31][C:28]2[CH:29]=[CH:30][C:25]([C:21]3[C:20]([CH3:33])=[C:19]([Cl:18])[N:23]([CH3:24])[N:22]=3)=[CH:26][C:27]=2[CH3:32])=[C:4]([N:11]2[C:15](=[O:16])[N:14]([CH3:17])[N:13]=[N:12]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 898762341-(2-Bromomethyl-3-methylthiophenyl)-4-methyl-1,4-dihydrotetrazol-5-oneHCID 1369523674-(5-Chloro-1,4-dimethyl-1H-pyrazol-3-yl)-2-methylphenol

Product 1

HCID 1182903911-{3-methylthio-2-[2-methyl-4-(5-chloro-1,4-dimethyl-1H-pyrazol-3-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(2-bromomethyl-3-methylthiophenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Preparation example 13) 1.5 g, 4-(5-chloro-1,4-dimethyl-1H-pyrazol-3-yl)-2-methyl-phenol 1 g, potassium carbonate 0.9 g and acetonitrile 20 ml was stirred with heating under reflux for five hours. The reaction mixture was concentrated and the resulting residue was subjected to a silica gel column chromatography to give 1-{3-methylthio-2-[2-methyl-4-(5-chloro-1,4-dimethyl-1H-pyrazol-3-yl)-phenoxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazole-5-one (hereinafter, referred to as “Present compound 38”) 2.1 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for five hours
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-dde7b5c1c0114613918e2e77e430b982
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

Loading…