Methane → HCID 54264315, compound

HRID 893960Notes

Reaction equation

HRID 893960 reaction equation
[C:1]([CH:3]1[CH2:5][NH:4]1)#[N:2].C1(C)C=CC=CC=1.[C:13]([N:23]=[C:24]=[O:25])(=[O:22])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C>C(OCC)(=O)C>[C:13]([NH:23][C:24]([N:4]1[CH2:5][CH:3]1[C:1]#[N:2])=[O:25])(=[O:22])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 1140Toluene2×HCID 118115Aziridine-2-carbonitrileHCID 54060928HCID 54060928, compound

Product 1

HCID 54264315HCID 54264315, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 0.98 g. 2-cyanoaziridine in 20 ml. toluene is added dropwise, while stirring, at 20° to 30° C. to 2.5 g. cinnamoyl isocyanate dissolved in 20 ml. toluene. The resultant suspension is stirred for 1 hour at ambient temperature, then filtered off with suction and washed with toluene. The crystals obtained are triturated with anhydrous diethyl ether and dried for 1 hour at 50° C. in a vacuum to give 1.9 g. of crude product; m.p. 134°-136° C. This crude product is boiled with 50 ml. ethyl acetate for a short time, mixed with active charcoal and then filtered. The hot ethyl acetate filtrate is evaporated in a vacuum and the evaporation residue triturated with anhydrous diethyl ether. There is thus obtained 1.2 g. 1-(N-cinnamoyl-carbamoyl)-2-cyanoaziridine; m.p. 163°-164° C. The compound is practically insoluble in water but goes into solution upon the addition of excess 2 N aqueous sodium hydroxide solution.

Workup

  1. filtrationfiltered off with suction
  2. washwashed with toluene
  3. customThe crystals obtained
  4. customare triturated with anhydrous diethyl ether
  5. customdried for 1 hour at 50° C. in a vacuum
  6. customto give 1.9 g
  7. filtrationfiltered
  8. customThe hot ethyl acetate filtrate is evaporated in a vacuum
  9. customthe evaporation residue triturated with anhydrous diethyl ether
  10. additiongoes into solution upon the addition of excess 2 N aqueous sodium hydroxide solution

Sources & evidence

ORD record
ord-72290f0f68e3419b8005407cbf7ffd4f
Source dataset
uspto-grants-1981_08
Patent number
US04282212

Reaction notes

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