Aziridine-2-carbonitrile → HCID 21161922, compound

HRID 893961Notes

Reaction equation

HRID 893961 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]([N:9]=[C:10]=[O:11])=[O:8])=[O:5])[CH3:2].[C:12]([CH:14]1[CH2:16][NH:15]1)#[N:13]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([CH2:6][C:7]([NH:9][C:10]([N:15]1[CH2:16][CH:14]1[C:12]#[N:13])=[O:11])=[O:8])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 118115Aziridine-2-carbonitrileHCID 21161918HCID 21161918, compound

Product 1

HCID 21161922HCID 21161922, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

4 g. Ethoxycarbonylacetyl isocyanate are dissolved in 40 ml. toluene and mixed, while stirring, at 20°-30° C. with a solution of 1.73 g. 2-cyanoaziridine in 20 ml. toluene. After about 5 minutes, an oily deposit separates out which, after trituration, gradually solidifies. The suspension thus obtained is further stirred for 1 hour at ambient temperature, then filtered off with suction and washed with toluene and the solid product triturated with anhydrous diethyl ether. There are thus obtained 3.7 g. 1-(N-ethoxycarbonylacetyl-carbamoyl)-2-cyanoaziridine; m.p. 121°-123° C. The product is practically insoluble in water but is soluble in dilute aqueous sodium hydroxide solution.

Workup

  1. customThe suspension thus obtained
  2. stirringis further stirred for 1 hour at ambient temperature
  3. filtrationfiltered off with suction
  4. washwashed with toluene
  5. customthe solid product triturated with anhydrous diethyl ether

Sources & evidence

ORD record
ord-12855aee429a4311bcfea65bde45ddc8
Source dataset
uspto-grants-1981_08
Patent number
US04282212

Reaction notes

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