Aziridine-2-carbonitrile → 1-(N-Cyclohexanecarbonyl-carbamoyl)-2-cyanoaziridine

HRID 893962Notes

Reaction equation

HRID 893962 reaction equation
[C:1]([CH:3]1[CH2:5][NH:4]1)#[N:2].[CH:6]1([C:12]([N:14]=[C:15]=[O:16])=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>C1(C)C=CC=CC=1>[CH:6]1([C:12]([NH:14][C:15]([N:4]2[CH2:5][CH:3]2[C:1]#[N:2])=[O:16])=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 118115Aziridine-2-carbonitrileHCID 20096062Cyclohexanecarbonyl isocyanate

Product 1

HCID 211620391-(N-Cyclohexanecarbonyl-carbamoyl)-2-cyanoaziridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 1.41 g. 2-cyanoaziridine in 20 ml. toluene is added dropwise, while stirring, at 20°-30° C. to a solution of 3.2 g. cyclohexanecarbonyl isocyanate in 50 ml. toluene. The reaction mixture is further stirred for 15 minutes at ambient temperature and a certain amount of greasy material which precipitates out is separated off. The clear solution is further stirred for 1 hour at ambient temperature and the crystals which have, in the meantime separated out, are filtered off with suction. They are washed with toluene, triturated with anhydrous diethyl ether and dried in a vacuum for 1 hour at 50° C. There are thus obtained 3.2 g. 1-(N-cyclohexanecarbonyl-carbamoyl)-2-cyanoaziridine; m.p. 142°-144° C. This compound is practically insoluble in water but dissolves in dilute aqueous sodium hydroxide solution.

Workup

  1. stirringThe reaction mixture is further stirred for 15 minutes at ambient temperature
  2. customa certain amount of greasy material which precipitates out
  3. customis separated off
  4. stirringThe clear solution is further stirred for 1 hour at ambient temperature
  5. customseparated out
  6. filtrationare filtered off with suction
  7. washThey are washed with toluene
  8. customtriturated with anhydrous diethyl ether
  9. customdried in a vacuum for 1 hour at 50° C
  10. dissolutiondissolves in dilute aqueous sodium hydroxide solution

Sources & evidence

ORD record
ord-3b06c343dc2445469c5a93f18bf927a1
Source dataset
uspto-grants-1981_08
Patent number
US04282212

Reaction notes

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