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

HRID 718645Notes

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.CCOCC>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

Conditions

Temperature: 95 °C

Procedure

To a solution of compound 51a (5.8 g, 23 mmol) in AcOH (20 mL) was added Br2 (7.3 g, 46 mmol) dropwise at 95° C. The reaction mixture was stirred for another 30 min at 95° C. and allowed to cool to rt. Et2O (100 mL) was added. The solids formed were collected by filtration and washed with Et2O (2×30 mL) to obtain compound 51b as a yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C9H8BrN3O: 254.0 (M+H). Found 254.1.

Workup

temperatureto cool to rt
customThe solids formed
filtrationwere collected by filtration
washwashed with Et2O (2×30 mL)

Sources & evidence

ORD record: ord-7bf44100fb174ae3867610b764c83633
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193736B2

Reaction notes

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