Aziridine-2-carbonitrile → HCID 21161947, compound

HRID 893956Notes

Reaction equation

HRID 893956 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([N:8]=[C:9]=[O:10])=[O:7].[C:11]([CH:13]1[CH2:15][NH:14]1)#[N:12]>C1(C)C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:8][C:9]([N:14]1[CH2:15][CH:13]1[C:11]#[N:12])=[O:10])=[O:7]

Participants

4

Reactant 2

HCID 118115Aziridine-2-carbonitrileHCID 126085392-Thiophenecarbonyl isocyanate

Product 1

HCID 21161947HCID 21161947, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2.76 g. Thiophene-2-carbonyl isocyanate are dissolved in 45 ml. anhydrous toluene and mixed dropwise, while stirring, at 20° to 30° C. with a solution of 1.22 g. 2-cyanoaziridine in 30 ml. toluene. Stirring is continued for 1 hour at ambient temperature and the precipitate obtained is filtered off with suction, washed with toluene and subsequently triturated with diethyl ether. There are thus obtained 3.4 g. 1-(N-2-thiophene-carbonyl-carbamoyl)-2-cyanoaziridine; m.p. 156°-160° C., which still contains a little thiophene-2-carboxylic acid amide.

Workup

  1. stirringStirring
  2. customthe precipitate obtained
  3. filtrationis filtered off with suction
  4. washwashed with toluene
  5. customsubsequently triturated with diethyl ether

Sources & evidence

ORD record
ord-86125920b2814ee88f415d6ae0b6b6b5
Source dataset
uspto-grants-1981_08
Patent number
US04282212

Reaction notes

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