4-Chloro-2-nitroaniline → HCID 22507051, compound

HRID 1368852Notes

Reaction equation

HRID 1368852 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[C:12](=[O:15])([O-])O.[Na+].[N:17]1[C:24](Cl)=[N:23][C:21](Cl)=[N:20][C:18]=1Cl.[CH3:26][O-:27].[Na+]>O1CCCC1.O>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:18]2[N:20]=[C:21]([O:27][CH3:26])[N:23]=[C:24]([O:15][CH3:12])[N:17]=2)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

7

Reactant 4

HCID 69794-Chloro-2-nitroanilineHCID 7954Cyanuric chlorideHCID 516892Sodium BicarbonateHCID 10942334Sodium Methoxide

Product 1

HCID 22507051HCID 22507051, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-2-nitroaniline (5.0 g) and sodium hydrogencarbonate (3.6 g) were dissolved in tetrahydrofuran (50 ml), and cyanuric chloride (8.0 g) was added thereto, followed by stirring for 8 hours. To the reaction solution, 28% sodium methylate (11.2 g) was added, followed by ref lux for 1 hour. Water was added thereto, followed by extraction with ethyl acetate, washing with a saturated sodium chloride aqueous solution and drying over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was subjected to recrystallization from ethanol to obtain 6.3 of the desired product as a yellow powder (m.p. 206-208° C.).

Workup

  1. waitfollowed by ref lux for 1 hour
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashing with a saturated sodium chloride aqueous solution
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was subjected to recrystallization from ethanol

Sources & evidence

ORD record
ord-5cddce8bffea4e6c8fdc8d12ea4f5b8c
Source dataset
uspto-grants-2003_06
Patent number
US06576631B1

Reaction notes

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