Brodimoprim → HCID 178488801, compound

HRID 2398069Notes

Reaction equation

HRID 2398069 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([Br:18])=[C:12]([O:19][CH3:20])[CH:11]=2)=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:29])C=1>O1CCOCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([Br:18])=[C:12]([O:19][CH3:20])[CH:11]=2)=[CH:4][N+:3]=1[O-:29]

Participants

4

Reactant 2

HCID 68760BrodimoprimHCID 70297m-Chloroperbenzoic acid2×

Product 1

HCID 178488801HCID 178488801, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.4 G. of 2,4-diamino-5-(4-bromo-3,5-dimethoxybenzyl)-pyrimidine were suspended in 40 ml. of dioxane and treated with 2.4 g. of 3-chloroperbenzoic acid with stirring. The temperature rose to 38° C. and, after 5 minutes (no more oxidizing agent was detectable), an additional 1.2 g. of 3-chloroperbenzoic acid were added. A clear solution resulted which, after stirring for 15 minutes, became cloudy. After 2 hours, the white precipitate was removed by filtration under vacuum, washed with a small amount of dioxane and recrystallized from ethanol, whereby there was obtained 2,4-diamino-5-(4-bromo-3,5-dimethoxybenzyl)-pyrimidine N1 -oxide of melting point 277°-278° C.

Workup

  1. customA clear solution resulted which
  2. waitAfter 2 hours
  3. customthe white precipitate was removed by filtration under vacuum
  4. washwashed with a small amount of dioxane
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3fb1e73ea4a24b82bdffbb0e8de73eb2
Source dataset
uspto-grants-1977_05
Patent number
US04024145

Reaction notes

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