Pyridine → HCID 21249784, compound

HRID 1531623Notes

Reaction equation

HRID 1531623 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].N1C=CC=CC=1.ClCCl.[CH3:25][CH:26]([CH3:33])[C:27]([O:29][CH2:30][CH2:31][OH:32])=[O:28]>O>[C:27]([O:29][CH2:30][CH2:31][O:32][C:7](=[O:8])[C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=1)(=[O:28])[CH:26]([CH3:33])[CH3:25]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 74323,5-Dinitrobenzoyl chloride2×HCID 813662-Hydroxyethyl isobutyrate

Product 1

HCID 21249784HCID 21249784, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

83 g ((0.36 mol) of 3,5-dinitrobenzoyl chloride (compound 2) and 28 g (0.36 mol) of pyridine were placed in a 1-l four-necked flask equipped with a dropping funnel, a reflux condenser, a thermometer and a mixing blade. Thereto was added 100 ml of dichloromethane for dissolution. The flask was cooled to 10° C. with ice water. Thereto was dropwise added, in 20 minutes with the temperature (10° C.) being maintained, 62 g (0.47 mol) of 2-hydroxyethyl 2-methylpropionate. After the dropwise addition, the flask was immersed in an oil bath of 50° C. and the flask contents were stirred for 1 hour. The flask was cooled to room temperature and 50 ml of water was added, followed by stirring for several minutes. All the flask contents were transferred into a separating funnel and the aqueous layer was separated to remove. The organic layer taken out was returned to the separating funnel. Thereto was added a 5% aqueous sodium carbonate solution, followed by mixing. The lower layer (organic layer) was taken out and dried over anhydrous magnesium sulfate. From the dried solution was removed dichloromethane by distillation by the use of an evaporator, whereby a solid was separated. The solid was recrystallized from a mixed solvent consisting of 200 ml of methanol and 100 ml of water to obtain 2-(3,5-dinitrobenzoyloxy)ethyl isobutyrate (compound 3). Yield: 100 g (86%) Melting point: 55-58° C.

Workup

  1. customequipped with a dropping funnel, a reflux condenser
  2. dissolutionfor dissolution
  3. additionThereto was dropwise added, in 20 minutes with the temperature (10° C.)
  4. temperaturebeing maintained
  5. additionAfter the dropwise addition
  6. customthe flask was immersed in an oil bath of 50° C.
  7. stirringby stirring for several minutes
  8. customAll the flask contents were transferred into a separating funnel
  9. customthe aqueous layer was separated
  10. customto remove
  11. additionThereto was added a 5% aqueous sodium carbonate solution
  12. additionby mixing
  13. dry with materialdried over anhydrous magnesium sulfate
  14. customFrom the dried solution was removed dichloromethane
  15. distillationby distillation
  16. customby the use of an evaporator, whereby a solid
  17. customwas separated
  18. customThe solid was recrystallized from a mixed solvent

Sources & evidence

ORD record
ord-9799073491004c9f9f3bebf04e26ae0e
Source dataset
uspto-grants-2001_03
Patent number
US06200831B1

Reaction notes

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