Sodium Methoxide → HCID 23335969, compound

HRID 903480Notes

Reaction equation

HRID 903480 reaction equation
Cl[C:2]1[C:3]([N+:16]([O-:18])=[O:17])=[C:4]([C:9]([N+:13]([O-:15])=[O:14])=[CH:10][C:11]=1[CH3:12])[NH:5][CH:6]([CH3:8])[CH3:7].[CH3:19][O-:20].[Na+]>CO>[CH:6]([NH:5][C:4]1[C:9]([N+:13]([O-:15])=[O:14])=[CH:10][C:11]([CH3:12])=[C:2]([O:20][CH3:19])[C:3]=1[N+:16]([O-:18])=[O:17])([CH3:8])[CH3:7]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 23335967HCID 23335967, compound

Product 1

HCID 23335969HCID 23335969, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 5.47 g. (0.02 mole) of 3-chloro-N-isopropyl-4-methyl-2,6-dinitroaniline in 100 ml. of methanol is added 1.79 g. (0.033 mole) of sodium methoxide. The reaction mixture is stirred at reflux for three hours, cooled to room temperature and filtered. The filtrate is evaporated at reduced pressure and the residue partitioned between ether and dilute aqueous hydrochloric acid. The organic phase is successively washed with water, saturated sodium bicarbonate and brine. It is then dried over anhydrous magnesium sulfate. Evaporation of the solvent in vacuo gives 5.0 g. of the desired product having a m.p. of 72°-77° C. Two recrystallizations from methanol give the analytical sample, m.p. 77.5°-79° C. Analysis: Calcd. for C11H15N3O5 : C, 49.07; H, 5.62; N, 15.61. Found: C, 49.35; H, 5.66; N, 15.77.

Workup

  1. temperatureat reflux for three hours
  2. filtrationfiltered
  3. customThe filtrate is evaporated at reduced pressure
  4. customthe residue partitioned between ether and dilute aqueous hydrochloric acid
  5. washThe organic phase is successively washed with water, saturated sodium bicarbonate and brine
  6. dry with materialIt is then dried over anhydrous magnesium sulfate
  7. customEvaporation of the solvent in vacuo
  8. customgives 5.0 g

Sources & evidence

ORD record
ord-48a4f67d438b4c6aba24a30abfdb06c0
Source dataset
uspto-grants-1980_10
Patent number
US04227913

Reaction notes

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