Aziridine-2-carbonitrile → HCID 21161967, compound

HRID 893964Notes

Reaction equation

HRID 893964 reaction equation
[C:1]([CH:3]1[CH2:5][NH:4]1)#[N:2].[CH2:6]1[O:19][C:18]2[CH:17]=[CH:16][C:10]([C:11]([N:13]=[C:14]=[O:15])=[O:12])=[CH:9][C:8]=2[O:7]1.C1OC2C=CC(C(N)=O)=CC=2O1>C1(C)C=CC=CC=1>[CH2:6]1[O:19][C:18]2[CH:17]=[CH:16][C:10]([C:11]([NH:13][C:14]([N:4]3[CH2:5][CH:3]3[C:1]#[N:2])=[O:15])=[O:12])=[CH:9][C:8]=2[O:7]1

Participants

5

Reactant 3

HCID 118115Aziridine-2-carbonitrileHCID 2303651,3-benzodioxole-5-carboxamideHCID 21202813HCID 21202813, compound

Product 1

HCID 21161967HCID 21161967, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

0.26 g. 2-Cyanoaziridine are dissolved in 5 ml. toluene and introduced, while stirring at 0° C., into a solution of 0.73 g. 3,4-methylenedioxybenzoyl isocyanate in 25 ml. toluene. The reaction mixture is further stirred for 1 hour at 0° C. and the precipitated material (0.65 g.) is filtered off with suction at ambient temperature and briefly boiled with isopropanol, 0.2 g. of the desired 1-(N-3,4-methylenedioxybenzoyl-carbamoyl)-2-cyanoaziridine thereby remaining undissolved (m.p. 145°-153° C., at 172° C. a clear melt is obtained). It is contaminated with a little 3,4-methylenedioxybenzamide.

Workup

  1. stirringThe reaction mixture is further stirred for 1 hour at 0° C.
  2. filtrationthe precipitated material (0.65 g.) is filtered off with suction at ambient temperature
  3. customat 172° C. a clear melt is obtained)

Sources & evidence

ORD record
ord-e1c7266a4dcb413680d5f1d2fdc9776f
Source dataset
uspto-grants-1981_08
Patent number
US04282212

Reaction notes

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