Diazomethane → HCID 20566541, compound

HRID 848238Notes

Reaction equation

HRID 848238 reaction equation
[N+](=[CH2:3])=[N-].[C:4]([N:7]1[CH:11]=[CH:10][N:9]([C:12](=[O:14])[CH3:13])[C:8]1=[O:15])(=[O:6])[CH3:5]>CCOCC.C(OCCCC)CCC>[C:12]([N:9]1[CH:10]=[CH:11][N:7]([C:4](=[O:6])[CH3:5])[C:8]1=[O:15])(=[O:14])[CH3:13].[C:12]([N:9]1[C:8](=[O:15])[N:7]([C:4](=[O:6])[CH3:5])[CH:11]2[CH:10]1[CH2:3]2)(=[O:14])[CH3:13]

Participants

6

Reactant 2

HCID 9550DiazomethaneHCID 11378721HCID 11378721, compound

Product 2

HCID 11378721HCID 11378721, compoundHCID 20566541HCID 20566541, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8909Butyl etherSolvent

Procedure

A solution of diazomethane in ether(prepared from 200 g of N-nitrosomethylurea) is introduced in portions over the course of 3 days into a solution of 25.0 g (0.15 mol) of 1,3-diacetyl-4-imidazolin-2-one and 5.0 g of copper-I chloride in 250 ml of di-n-butyl ether at 80°-90°. The solution is then filtered, the residue is repeatedly eluted with benzene and the combined filtrates are concentrated in vacuo. Chromatography of the crude product on silica gel gives 10.3 g of unconverted 1,3-diacetyl-4-imidazolin-2-one and 3.6 g (about 20%) of 2,4-diacetyl-2,4-diaza-bicyclo[3,1,0]hexan-3-one as colourless crystals of melting point 134°-136° C. (from ether).

Workup

  1. filtrationThe solution is then filtered
  2. washthe residue is repeatedly eluted with benzene
  3. concentrationthe combined filtrates are concentrated in vacuo

Sources & evidence

ORD record
ord-c464c74e4e494fda83604d052727b36b
Source dataset
uspto-grants-1981_10
Patent number
US04294973

Reaction notes

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