N-bromobutanimide → HCID 86589888, compound

HRID 2417534Notes

Reaction equation

HRID 2417534 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6].C1C(C(OO)=O)=CC=CC=1.BrN1C(=O)CCC1=O.Cl.[CH2:32]([O:34][C:35](=[O:38])[CH2:36][NH2:37])[CH3:33].C(=O)([O-])O.[Na+]>C(O)C.C(OCC)(=O)C.C1C=CC=CC=1>[C:5]([C:4]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([CH:3]=1)[CH2:1][NH:37][CH2:36][C:35]([O:34][CH2:32][CH3:33])=[O:38])#[N:6]

Participants

9

Reactant 5

HCID 67184N-bromobutanimide3×HCID 516892Sodium BicarbonateHCID 523077Perbenzoic acid3×HCID 2723640Glycine ethyl ester, hydrochlorideHCID 28014343-Methyl-4-nitrobenzonitrile

Product 1

HCID 86589888HCID 86589888, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

4.0 g (24.6 mmol) of 3-methyl-4-nitrobenzonitrile was added to a mixture of 100 ml of benzene, 100 ml of perbenzoic acid and 5.3 g (29 mmol) of N-bromosuccinimide, and they were heated under reflux for 2 days. 100 mg of perbenzoic acid and 4.0 g (22.5 mmol) of N-bromosuccinimide were added to the reaction mixture, and they were heated under reflux for 2 days. Thereafter, 100 mg of perbenzoic acid and 4.0 g (22.5 mmol) of N-bromosuccinimide were added to the reaction mixture, and they were heated under reflux for 2 days. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 50 ml of ethanol. 6.9 g (49.2 mmol) of glycine ethyl ester hydrochloride and 6.2 g (73.8 mmol) of sodium hydrogencarbonate were added to the obtained solution, and they were stirred at 70° C. for 6 hours. The solvent was evaporated. After the extraction with ethyl acetate, the extract was washed with 1 N hydrochloric acid. The obtained aqueous layer was made basic with 1 N sodium hydroxide. After the extraction with ethyl acetate, the obtained organic layer was washed with saturated aqueous sodium chloride solution and then dried. The solvent was evaporated to obtain the title compound.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 2 days
  3. temperaturewere heated
  4. temperatureunder reflux for 2 days
  5. temperaturewere heated
  6. temperatureunder reflux for 2 days
  7. customThe solvent was evaporated
  8. extractionAfter the extraction with ethyl acetate
  9. washthe extract was washed with 1 N hydrochloric acid
  10. extractionAfter the extraction with ethyl acetate
  11. washthe obtained organic layer was washed with saturated aqueous sodium chloride solution
  12. customdried
  13. customThe solvent was evaporated

Sources & evidence

ORD record
ord-bc87261569d648c8bc264a30c7ba7d4a
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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