Bromine → 3-(4-Bromophenyl)-1-methyl-4,5-dihydro-1H-1,2,4-triazol-5-one

HRID 1772606Notes

Reaction equation

HRID 1772606 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[N:9]/[N:10]([CH3:14])[C:11]([NH2:13])=[O:12])=[CH:4][CH:3]=1.BrBr>CC(O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:13][C:11](=[O:12])[N:10]([CH3:14])[N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 1177279021-[(E)-(4-bromophenyl)methylideneamino]-1-methylurea

Product 1

HCID 1369420733-(4-Bromophenyl)-1-methyl-4,5-dihydro-1H-1,2,4-triazol-5-oneYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of compound 10a (5.80 g, 22.6 mmol) in AcOH (20 mL), was added Br2 (7.30 g, 45.7 mmol) dropwise. The reaction mixture was stirred at 95° C. for 30 min. After cooling to rt, the product was precipitated by addition of Et2O and collected by filtration and washed with Et2O to obtain compound 10b as a yellow solid (5.50 g, 96% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C9H8BrN3O: 254.0 (M+H). Found 254.1.

Workup

  1. temperatureAfter cooling to rt
  2. customthe product was precipitated by addition of Et2O
  3. filtrationcollected by filtration
  4. washwashed with Et2O

Sources & evidence

ORD record
ord-d8090a075fba402597d5bdddcad8c062
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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