Aziridine-2-carbonitrile → HCID 21161953, compound

HRID 893955Notes

Reaction equation

HRID 893955 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([N:9]=[C:10]=[O:11])=[O:8])([O-:3])=[O:2].[C:15]([CH:17]1[CH2:19][NH:18]1)#[N:16]>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([NH:9][C:10]([N:18]1[CH2:19][CH:17]1[C:15]#[N:16])=[O:11])=[O:8])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 118115Aziridine-2-carbonitrileHCID 125834393-Nitrobenzoyl isocyanate

Product 1

HCID 21161953HCID 21161953, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 5.8 g. m-nitrobenzoyl isocyanate in 100 ml. toluene is added dropwise, while stirring, in the course of about 10 minutes to 2.04 g. 2-cyanoaziridine in 50 ml. anhydrous toluene. The reaction mixture is stirred for 30 minutes at ambient temperature and the precipitated solid product is filtered off with suction, washed with toluene and triturated with diethyl ether. There are thus obtained 4.8 g. white 1-(N-3-nitrobenzoyl-carbamoyl)-2-cyanoaziridine; m.p. 156°-158° C. (after drying for 1.5 hours in a vacuum at 70° C.).

Workup

  1. stirringThe reaction mixture is stirred for 30 minutes at ambient temperature
  2. filtrationthe precipitated solid product is filtered off with suction
  3. washwashed with toluene
  4. customtriturated with diethyl ether
  5. customm.p. 156°-158° C. (after drying for 1.5 hours in a vacuum at 70° C.)

Sources & evidence

ORD record
ord-66f58a829eb44adf81a2bca09b820276
Source dataset
uspto-grants-1981_08
Patent number
US04282212

Reaction notes

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