Dichloromethane → HCID 178448864, compound

HRID 2276767Notes

Reaction equation

HRID 2276767 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:19])([CH3:18])[CH2:9][NH:10][C:11]2[N+:12]([O-:17])=[N:13][CH:14]=[CH:15][N:16]=2)=[CH:4][CH:3]=1.ClCCl.[Br:23]Br>CC#N>[Br:23][C:14]1[N:13]=[N+:12]([O-:17])[C:11]([NH:10][CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)([CH3:19])[CH3:18])=[N:16][CH:15]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24408BromineHCID 178448869HCID 178448869, compound

Product 1

HCID 178448864HCID 178448864, compoundYield 59.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(2-(4-fluorophenyl)-2-methylpropyl)-1,2,4-triazin-3-amine-2-oxide (1.2 g, 7.4 mmol) in a 1:1 mixture of dichloromethane and CH3CN (40 mL) was added Br2 (1.0 mL, 19 mmol). The mixture was stirred at room temperature for 72 h. The solvents were evaporated and the residue was dissolved in ether. The solution was filtered through a plug of silica gel and the solvents evaporated to give the desired product (1.5 g, 58%) as an orange sticky solid.

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue was dissolved in ether
  3. filtrationThe solution was filtered through a plug of silica gel
  4. customthe solvents evaporated

Sources & evidence

ORD record
ord-285cc70d51314c7aa067c5e74218aba0
Source dataset
uspto-grants-2015_09
Patent number
US09133123B2

Reaction notes

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