Ethyl Acetate → HCID 23297982, compound

HRID 1953786Notes

Reaction equation

HRID 1953786 reaction equation
Br[CH2:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]2[C:4]=1[N:5]=[C:6]([O:18][CH3:19])[C:7]([O:16][CH3:17])=[N:8]2.Cl.[CH2:21]([NH:28][CH2:29][P:30]([O:35][CH2:36][CH3:37])(=[O:34])[O:31][CH2:32][CH3:33])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(C(C)C)C(C)C)C.C(OCC)(=O)C>CN(C)C=O>[CH2:21]([N:28]([CH2:29][P:30](=[O:34])([O:35][CH2:36][CH3:37])[O:31][CH2:32][CH3:33])[CH2:2][C:3]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]2[C:4]=1[N:5]=[C:6]([O:18][CH3:19])[C:7]([O:16][CH3:17])=[N:8]2)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 232979835-Bromomethyl-7-nitro-2,3-dimethoxyquinoxalineHCID 23298000HCID 23298000, compound

Product 1

HCID 23297982HCID 23297982, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g (3.05 mmol) of 5-bromomethyl-2,3-dimethoxy-7-nitroquinoxaline, 1.1 g (3.66 mmol) of diethyl benzylaminomethanephosphonate hydrochloride and 1.9 ml (10.98 mmol) of N-ethyldiisopropylamine are stirred at room temperature for about 18 hours and at 80° C. for a further 3 hours in 10 ml of dimethylformamide under argon. After addition of ethyl acetate, the mixture is extracted with water and brine, the aqueous phases are washed with ethyl acetate, and the organic phases are combined, dried using sodium sulfate, filtered on a suction filter and concentrated. The evaporation residue is chromatographed on silica gel using hexane-ethyl acetate (1:1). 0.71 g (46%) of diethyl N-benzyl-N-(2,3-dimethoxy-7-nitroquinoxalin-5-ylmethyl)aminomethylphosphonate is obtained.

Workup

  1. extractionthe mixture is extracted with water and brine
  2. washthe aqueous phases are washed with ethyl acetate
  3. customdried
  4. filtrationfiltered on a suction
  5. filtrationfilter
  6. concentrationconcentrated
  7. customThe evaporation residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-b9a0b7b151f94feb9b2830aa373ecb1d
Source dataset
uspto-grants-2000_09
Patent number
US06117873

Reaction notes

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