Propionyl chloride → HCID 23461523, compound

HRID 2286572Notes

Reaction equation

HRID 2286572 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[C:6]([CH:8]1[CH2:10][NH:9]1)#[N:7].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C(OCC)C.C(N(CC)CC)C>[C:1]([N:9]1[CH2:10][CH:8]1[C:6]#[N:7])(=[O:4])[CH2:2][CH3:3]

Participants

7

Reactant 3

HCID 62324Propionyl chlorideHCID 118115Aziridine-2-carbonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 23461523HCID 23461523, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolvent2×HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 0.92 g. propionyl chloride in 40 ml. anhydrous diethyl ether is added dropwise at 0° to 5° C., in the course of about 15 minutes, to a solution of 0.68 g. 2-cyanoaziridine and 1.2 g. triethylamine in 40 ml. anhydrous diethyl ether. The reaction mixture is stirred for 1 hour at 0° C. and then for 2 hours at ambient temperature. The precipitated salt is filtered off with suction and washed with diethyl ether into the filtrate and the filtrate is evaporated in a vacuum to give 1.44 g. of an oil. This is dissolved in ethyl acetate, shaken with a saturated aqueous solution of sodium bicarbonate, dried and then evaporated in a vacuum. There is thus obtained 1.14 g. 1-propionyl-2-cyanoaziridine in the form of a pale oil, the analytical data (elementary analysis, NMR and mass spectra) of which confirm the structure. The product is slightly contaminated with water.

Workup

  1. waitfor 2 hours at ambient temperature
  2. filtrationThe precipitated salt is filtered off with suction
  3. washwashed with diethyl ether into the filtrate
  4. customthe filtrate is evaporated in a vacuum
  5. customto give 1.44 g
  6. customdried
  7. customevaporated in a vacuum

Sources & evidence

ORD record
ord-cf1ef420dde749a898fa5a00c3784f9f
Source dataset
uspto-grants-1981_05
Patent number
US04267174

Reaction notes

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