Aziridine → 1-(4-Fluoro-2-nitrobenzoyl)aziridine

HRID 437620Notes

Reaction equation

HRID 437620 reaction equation
[NH:1]1[CH2:3][CH2:2]1.C(=O)([O-])O.[Na+].[F:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[C:12]([N+:19]([O-:21])=[O:20])[CH:11]=1.[OH-].[Na+]>ClC(Cl)Cl>[F:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([N:1]2[CH2:3][CH2:2]2)=[O:15])=[C:12]([N+:19]([O-:21])=[O:20])[CH:11]=1

Participants

6

Reactant 4

HCID 9033AziridineHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 133524084-Fluoro-2-nitrobenzoyl chloride

Product 1

HCID 214288531-(4-Fluoro-2-nitrobenzoyl)aziridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 21.6 parts of aziridine and 37.8 parts of sodium hydrogen carbonate is added dropwise a solution of 85 parts of 4-fluoro-2-nitro benzoyl chloride in 75 parts of trichloromethane while stirring vigorously at 0° C. Upon completion, stirring vigorously is continued for 30 minutes without cooling. After warming to 25° C, the reaction mixture is adjusted to pH 8 with a diluted sodium hydroxide solution. The product is extracted three times with trichloromethane. The combined extracts are washed with water, dried filtered and evaporated, yielding 75 parts of 1-(4-fluoro-2-nitrobenzoyl)aziridine as a residue.

Workup

  1. stirringUpon completion, stirring vigorously
  2. temperaturewithout cooling
  3. temperatureAfter warming to 25° C
  4. extractionThe product is extracted three times with trichloromethane
  5. washThe combined extracts are washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-2f24b8dc59c74dd2b9e37593baa1f60a
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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