N-bromobutanimide → HCID 86589872, compound

HRID 2417484Notes

Reaction equation

HRID 2417484 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C1C(C(OO)=O)=CC=CC=1.BrN1C(=O)CCC1=O.Cl.[CH2:31]([O:33][C:34](=[O:37])[CH2:35][NH2:36])[CH3:32].C(=O)([O-])O.[Na+]>C1C=CC=CC=1.C(O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:36][CH2:35][C:34]([O:33][CH2:31][CH3:32])=[O:37])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

9

Reactant 5

HCID 67184N-bromobutanimideHCID 1235464-Bromo-2-nitrotolueneHCID 516892Sodium BicarbonateHCID 523077Perbenzoic acidHCID 2723640Glycine ethyl ester, hydrochloride

Product 1

HCID 86589872HCID 86589872, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

19.8 g (91 mmol) of 4-bromo-2-nitrotoluene was dissolved in 150 ml of benzene. 50 mg of perbenzoic acid and 19.6 g (91 mmol) of N-bromosuccinimide were added to the obtained solution, and they were stirred at 80° C. for 2 days. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 100 ml of ethanol. 12.9 g (91 mmol) of glycine ethyl ester hydrochloride and 15.3 g (182 mmol) of sodium hydrogencarbonate were added to the obtained solution, and they were stirred at 80° C. for 4 hours. The insoluble matter was filtered out, and the solvent was evaporated. After the extraction with ethyl acetate, the obtained product 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. stirringwere stirred at 80° C. for 4 hours
  2. filtrationThe insoluble matter was filtered out
  3. customthe solvent was evaporated
  4. extractionAfter the extraction with ethyl acetate
  5. washthe obtained product was washed with 1 N hydrochloric acid
  6. extractionAfter the extraction with ethyl acetate
  7. washthe obtained organic layer was washed with saturated aqueous sodium chloride solution
  8. customdried
  9. customThe solvent was evaporated

Sources & evidence

ORD record
ord-34c3df5d4f884e419ee69459c04ff84f
Source dataset
uspto-grants-2004_11
Patent number
US06825191B2

Reaction notes

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