Chlorobenzene → 1-(2-Bromomethyl-3-methylthiophenyl)-4-methyl-1,4-dihydrotetrazol-5-one

HRID 628500Notes

Reaction equation

HRID 628500 reaction equation
[CH3:1][C:2]1[C:7]([S:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[N:13]([CH3:16])[N:12]=[N:11]1.N(C1(C#N)CCCCC1)=NC1(C#N)CCCCC1.[Br:35]N1C(=O)CCC1=O.ClC1C=CC=CC=1>O>[Br:35][CH2:1][C:2]1[C:7]([S:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N:10]1[C:14](=[O:15])[N:13]([CH3:16])[N:12]=[N:11]1

Participants

6

Reactant 4

HCID 7964ChlorobenzeneHCID 67184N-bromobutanimideHCID 749781,1'-Azobis(cyclohexanecarbonitrile)HCID 898759531-(2-Methyl-3-methylsulfanylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one

Product 1

HCID 898762341-(2-Bromomethyl-3-methylthiophenyl)-4-methyl-1,4-dihydrotetrazol-5-oneYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1-(2-methyl-3-methylsulfanylphenyl)-4-methyl-1,4-dihydrotetrazole-5-one (described in Reference Preparation example 15) 1.50 g, 1,1′-azobis(cyclohexane-1-carbonitrile) 0.620 g, N-bromosuccinimide 1.30 g and chlorobenzene 15 ml was stirred with heating under reflux for four hours. After cooling the mixture, to the reaction solutions was added water and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and was dried over anhydrous magnesium sulfate and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 1-(2-bromomethyl-3-methylthiophenyl)-4-methyl-1,4-dihydrotetrazole-5-one 0.400 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for four hours
  3. temperatureAfter cooling the mixture
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated saline
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-60beef1e4db14a8d91f2690ffa31a23a
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

Loading…