Bromine → HCID 23003182, compound

HRID 396159Notes

Reaction equation

HRID 396159 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8][O:9][C:10]2[N:11]=[C:12]3[C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[N:16][N:15]=[C:14]([CH3:24])[N:13]3[CH:25]=2)=[N:6][CH:5]=[N:4]1)[CH3:2].[Br:26]Br>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[Br:26][C:25]1[N:13]2[C:14]([CH3:24])=[N:15][N:16]=[C:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:12]2=[N:11][C:10]=1[O:9][CH2:8][C:7]1[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][N:6]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 23003177HCID 23003177, compound

Product 1

HCID 23003182HCID 23003182, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 2-(2-ethyl-2H-[1,2,4]triazol-3-ylmethoxy)-5-methyl-8-phenylimidazo[1,2-d][1,2,4]triazine (205 mg, 0.61 mmol) in a mixture of carbon tetrachloride (100 ml) and chloroform (50 ml) was added bromine (34.2 μl, 0.67 mmol) dropwise. The mixture was stirred for 1 h, the solvent removed in vacuo and the residue recrystallised from a mixture of diethyl ether and methanol to give the title compound (160 mg). δH (400 MHz; d6-DMSO) 1.35 (3H, t, J 7.2), 3.15 (3H, d, J 6.6), 4.31 (2H, q, J 7.2), 5.72 (2H, s), 7.58 (3H, m), 7.98 (1H, s), 8.42 (2H, m); m/z (ES+) 414/416 (M++H).

Workup

  1. customthe solvent removed in vacuo
  2. customthe residue recrystallised from a mixture of diethyl ether and methanol

Sources & evidence

ORD record
ord-9e4cf0bd065f4e2a82b3c6110a772317
Source dataset
uspto-grants-2003_08
Patent number
US06608062B1

Reaction notes

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