Dimethylformamide → HCID 10357193, compound

HRID 1378767Notes

Reaction equation

HRID 1378767 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].O.[NH2:13][CH:14](C(O)=O)[CH2:15][CH2:16][C:17]([OH:19])=[O:18].[C:23](=[O:26])([O-])[O-].[K+].[K+].[CH3:29]I.CN([CH:34]=[O:35])C>O.C(O)C>[CH3:23][O:26][C:34](=[O:35])[CH:14]([CH2:15][CH2:16][C:17]([O:19][CH3:29])=[O:18])[NH:13][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 118992,4-DichloronitrobenzeneHCID 16219385DL-Glutamic acid monohydrate

Product 1

HCID 10357193HCID 10357193, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 1-fluoro-2-nitrobenzene (VII, 4.80 g), DL-glutamic acid hydrate (XIIa, 5.62 g), potassium carbonate (8.00 g), ethanol (50 ml) and water (10 ml) is heated at 105° for 24 hr. The reaction mixture is then stripped of solvents and the residue stirred in DMF with methyl iodide (4 ml). After about a week, the DMF is removed and the residue is partitioned between dichloromethane and water. Silica gel chromatography (500 ml) using ethyl acetate/hexane (30/70) gives the title compound, NMR (CDCl3) 2.28, 2.51, 3.69, 3.79, 4.40, 6.73, 6.80, 7.45, 8.20 and 8.33 δ.

Workup

  1. temperatureis heated at 105° for 24 hr
  2. waitAfter about a week
  3. customthe DMF is removed
  4. customthe residue is partitioned between dichloromethane and water

Sources & evidence

ORD record
ord-8203a57b4bc4435c832b9005bb9319db
Source dataset
uspto-grants-1997_09
Patent number
US05668282

Reaction notes

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