Hydrogen Bromide → 5-bromo-1,2 dihydro-2,2-dimethyl-6-(2-imidazolin-2-ylamino)-3-(4H)-quinoxalinone

HRID 1614548Notes

Reaction equation

HRID 1614548 reaction equation
Br.[NH2:2][C:3]1[C:4]([Br:16])=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH3:14])([CH3:13])[C:7](=[O:15])[NH:6]2.[NH:17]1[CH2:21][CH2:20][N:19]=[C:18]1S(O)(=O)=O.Br>C(O)C(C)C>[Br:16][C:4]1[C:3]([NH:2][C:18]2[NH:19][CH2:20][CH2:21][N:17]=2)=[CH:12][CH:11]=[C:10]2[C:5]=1[NH:6][C:7](=[O:15])[C:8]([CH3:13])([CH3:14])[NH:9]2

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 2745614,5-dihydro-1H-imidazole-2-sulfonic acidHCID 199364056-Amino-5-bromo-1,2-dihydro-2,2-dimethyl-3-(4h)-quinoxalinone hydrobromide

Product 1

HCID 152257155-bromo-1,2 dihydro-2,2-dimethyl-6-(2-imidazolin-2-ylamino)-3-(4H)-quinoxalinone

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Procedure

A mixture of 6-amino-5-bromo-1,2-dihydro-2,2-dimethyl-3-(4H) - quinoxalinone hydrobromide (479 mg, 1 mmol) and 2-imidazoline-2-sulfonic acid (224 mg, 1.5 mmol) in isobutanol (5 ml) is heated at reflux until the starting hydrobromide material is consumed. The solvent is removed in vacuo and the residue chromatographed on silica gel with CHCl3 : CH3OH saturated with NH3 (g) elution to yield the title compound.

Workup

  1. temperatureis heated
  2. customis consumed
  3. customThe solvent is removed in vacuo
  4. customthe residue chromatographed on silica gel with CHCl3
  5. washCH3OH saturated with NH3 (g) elution

Sources & evidence

ORD record
ord-5e284c4625ad4d8ca1c9e107b11db3fd
Source dataset
uspto-grants-1993_03
Patent number
US05198442

Reaction notes

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