Water → HCID 178418916, compound

HRID 11197Notes

Reaction equation

HRID 11197 reaction equation
[OH:1][C:2]1[N:3]2[C:7]([N:8]=[C:9]([CH3:11])[CH:10]=1)=[N:6][CH:5]=[N:4]2.[Br:12]Br.O>C(O)(=O)C>[Br:12][C:10]1[C:9]([CH3:11])=[N:8][C:7]2[N:3]([N:4]=[CH:5][N:6]=2)[C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 178419009HCID 178419009, compound

Product 1

HCID 178418916HCID 178418916, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A suspension of 4-hydroxy-6-methyl-1,3,3a,7-tetraazaindene (15.0 g, 0.1 mol) in acetic acid (100 ml) was treated dropwise at 20° C. with a solution of bromine (16.172 g, 0.102 mol) in acetic acid (20 ml). As the reaction progressed, the suspended crystals dissolved and new crystals of brominated product were formed. After about 2 hours, the reaction mixture was poured into water (250 ml) and crystals were collected by filtration. The crude product was purified by first converting into its sodium salt by dissolving 22 g in one liter of hot aqueous 0.2N sodium carbonate and then slowly acidifying with dilute hydrochloric acid. The unchanged starting material was converted into a soluble salt by addition of excess of triethylamine. Crystals were then collected and recrystallized from hot water to give 19 g (82%) of Compound TAI-4 as white needles, m.p.=269° C.

Workup

  1. dissolutionthe suspended crystals dissolved
  2. customnew crystals of brominated product were formed
  3. filtrationwere collected by filtration
  4. customThe crude product was purified
  5. dissolutionby dissolving 22 g in one liter of hot aqueous 0.2N sodium carbonate
  6. additionwas converted into a soluble salt by addition of excess of triethylamine
  7. customCrystals were then collected
  8. customrecrystallized from hot water

Sources & evidence

ORD record
ord-a1674ca12e1f4271b7def85a3223021c
Source dataset
uspto-grants-2006_08
Patent number
US07097963B1

Reaction notes

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