Acetoin → HCID 15907880, compound

HRID 1359499Notes

Reaction equation

HRID 1359499 reaction equation
[NH2:1][C:2]1[C:7]([Br:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][C:3]=1[Br:13].O[CH:15]([CH3:19])[C:16](=O)[CH3:17].[C:20](#[N:24])[CH2:21][C:22]#[N:23]>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[NH2:23][C:22]1[N:1]([C:2]2[C:3]([Br:13])=[CH:4][C:5]([C:9]([F:12])([F:10])[F:11])=[CH:6][C:7]=2[Br:8])[C:15]([CH3:19])=[C:16]([CH3:17])[C:21]=1[C:20]#[N:24]

Participants

6

Reactant 3

HCID 179AcetoinHCID 8010MalononitrileHCID 1445654-Amino-3,5-dibromobenzotrifluoride

Product 1

HCID 15907880HCID 15907880, compoundYield 15.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

In 15 ml of toluene, 5.5 g of 4-amino-3,5-dibromobenzotrifluoride, 1.9 g of acetoin, and 34 mg of p-toluenesulfonic acid were dissolved. The reaction solution was heated under reflux for 2.5 hours while conducting azeotropic dehydration. To the reaction mixture, 1.42 g of malononitrile was added. The reaction mixture was heated for 4 hours while being concentrated at 180° C. Water was added to the reaction mixture. The reaction mixture was extracted with chloroform, and subsequently, the extract was dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=5:1), and was allowed to stand for crystallization to yield 1.2 g of 2-amino-4,5-dimethyl-l-(2,6-dibromo-4-trifluoromethylphenyl)pyrrole-3-carbonitrile.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureunder reflux for 2.5 hours
  3. temperatureThe reaction mixture was heated for 4 hours
  4. concentrationwhile being concentrated at 180° C
  5. additionWater was added to the reaction mixture
  6. extractionThe reaction mixture was extracted with chloroform
  7. dry with materialsubsequently, the extract was dried over anhydrous sodium sulfate
  8. filtrationAfter the desiccant was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=5:1)
  11. customto stand for crystallization

Sources & evidence

ORD record
ord-e993362598944b0bb6d4b4dbce2189dc
Source dataset
uspto-grants-2003_07
Patent number
US06600038B1

Reaction notes

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