Aziridine → HCID 21428907, compound

HRID 437646Notes

Reaction equation

HRID 437646 reaction equation
[NH:1]1[CH2:3][CH2:2]1.C(=O)([O-])O.[Na+].[Cl:9][C:10]1[C:11]([N+:21]([O-:23])=[O:22])=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:18]=1)[C:15](Cl)=[O:16].[OH-].[Na+]>O.ClC(Cl)Cl>[Cl:9][C:10]1[C:11]([N+:21]([O-:23])=[O:22])=[CH:12][C:13]([O:19][CH3:20])=[C:14]([CH:18]=1)[C:15]([N:1]1[CH2:3][CH2:2]1)=[O:16]

Participants

7

Reactant 4

HCID 9033AziridineHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 214289115-Chloro-2-methoxy-4-nitrobenzoyl chloride

Product 1

HCID 21428907HCID 21428907, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

To 230 parts of a solution of aziridine in water 0.875M are added 15 parts of sodium hydrogen carbonate while cooling at 0° C. Then there is added dropwise, during a 45 minutes-period, a solution of 42.5 parts of 5-chloro-2-methoxy-4-nitrobenzoyl chloride in 150 parts of trichloromethane at 0° C and while stirring vigorously. The mixture is diluted with about 150 parts of trichloromethane and the whole is stirred for 45 minutes without cooling. The reaction mixture is alkalized to pH 8 with a diluted sodium hydroxide solution. The product is extracted three times with trichloromethane. The combined extracts are washed three times with water, dried, filtered and evaporated, yielding 40 parts of 1-(5-chloro-2-methoxy-4-nitrobenzoyl)aziridine.

Workup

  1. additionThen there is added dropwise, during a 45 minutes-period
  2. temperaturewithout cooling
  3. extractionThe product is extracted three times with trichloromethane
  4. washThe combined extracts are washed three times with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-79bcea7f1d884e8790e68d820613a4a5
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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