Bromine → HCID 19421441, compound

HRID 744028Notes

Reaction equation

HRID 744028 reaction equation
[CH2:1]([O:3][P:4]([CH:9]([C:11]1[N:15]2[C:16]3[C:21]([NH:22][C:23](=[O:24])[C:14]2=[N:13][N:12]=1)=[CH:20][C:19]([C:25]([F:28])([F:27])[F:26])=[CH:18][CH:17]=3)[CH3:10])([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[Br:29]Br>S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Ag+2]>[Br:29][C:18]1[CH:17]=[C:16]2[C:21]([NH:22][C:23](=[O:24])[C:14]3[N:15]2[C:11]([CH:9]([P:4]([O:3][CH2:1][CH3:2])([O:6][CH2:7][CH3:8])=[O:5])[CH3:10])=[N:12][N:13]=3)=[CH:20][C:19]=1[C:25]([F:27])([F:26])[F:28]

Participants

5

Reactant 2

HCID 24408BromineHCID 19421403HCID 19421403, compound

Product 1

HCID 19421441HCID 19421441, compoundYield 53.3%

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 1-[1-(diethoxyphosphoryl)ethyl]-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one (811 mg, 1.94 mmol), silver sulfate (605 mg, 1.94 mmol) and bromine (100 μl, 1.94 mmol) in 5 ml of conc. sulfuric acid was stirred overnight at room temperature. The mixture was filtered and the filtrate was added dropwise to 100 ml of ice/water. The resulting precipitate was isolated by filtration, washed with water and dried to give 514 mg (53%) of the title compound; m.p.>200° C., decomp. 1H-NMR (DMSO-d6): δ 1.12 (t, 3H), 1.18 (t, 3H), 1.74 (dd, 3H), 3.95 (quint, 2H), 4.07 (quint, 2H), 4.78 (dq, 1H), 7.81 (s, 1H), 8.59 (s, 1H), 12.35 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was added dropwise to 100 ml of ice/water
  3. customThe resulting precipitate was isolated by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-69a8b1a661174e39ac1809cba0920a84
Source dataset
uspto-grants-1996_09
Patent number
US05559106

Reaction notes

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