Bromine → HCID 19352213, compound

HRID 1650091Notes

Reaction equation

HRID 1650091 reaction equation
[CH:1]([C:4]([CH3:14])([N:7]1[C:11](=[O:12])[CH:10]=[CH:9][C:8]1=[O:13])[C:5]#[N:6])([CH3:3])[CH3:2].[Br:15]Br>C(O)(=O)C>[Br:15][C:9]1[C:8](=[O:13])[N:7]([C:4]([CH:1]([CH3:3])[CH3:2])([CH3:14])[C:5]#[N:6])[C:11](=[O:12])[CH:10]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 13730721HCID 13730721, compound

Product 1

HCID 19352213HCID 19352213, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of α-isopropyl-α-methyl-2,5-dioxo-3-pyrroline-1-acetonitrile (50 g, 0.25 mol) in acetic acid (500 ml) heated at 75° C. is added bromine (40.76 g, 0.255 mol) in acetic acid (80 ml) dropwise with stirring. The reaction is maintained at 85° overnight and evaporated to a syrup, which is dissolved in methylene chloride (300 ml), is cooled to 5° C. to which triethylamine (34.78 ml) is added. After stirring for 2 hours the brown methylene chloride solution is diluted with ether and a white precipitate is formed. This is extracted with water (400 ml) and the organic layer is dried over anhydrous magnesium sulfate, then passed through a 2 inch bed of silica gel with methylene chloride to elute. The eluate is obtained as a dark brown oil. Anal. calcd. for C10H10N2O2Br: C, 44.29; H, 4.09; N, 10.33. Found: C, 43.37; H, 4.05; N, 10.07.

Workup

  1. temperatureThe reaction is maintained at 85° overnight
  2. customevaporated to a syrup, which
  3. dissolutionis dissolved in methylene chloride (300 ml)
  4. additionis added
  5. stirringAfter stirring for 2 hours the brown methylene chloride solution
  6. additionis diluted with ether
  7. customa white precipitate is formed
  8. extractionThis is extracted with water (400 ml)
  9. dry with materialthe organic layer is dried over anhydrous magnesium sulfate
  10. washto elute
  11. customThe eluate is obtained as a dark brown oil

Sources & evidence

ORD record
ord-0fd9adee2df944739bec4789ffe24b7f
Source dataset
uspto-grants-1990_05
Patent number
US04923504

Reaction notes

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