Dicyclohexylcarbodiimide → HCID 23461463, compound

HRID 2286567Notes

Reaction equation

HRID 2286567 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([C:7]([NH:9][CH2:10][C:11]([OH:13])=O)=[O:8])=[CH:3][CH:2]=1.[C:15]([CH:17]1[CH2:19][NH:18]1)#[N:16].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH3:14][C:1]1[CH:2]=[CH:3][C:4]([C:7]([NH:9][CH2:10][C:11]([N:18]2[CH2:19][CH:17]2[C:15]#[N:16])=[O:13])=[O:8])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 97479p-Methylhippuric acidHCID 118115Aziridine-2-carbonitrile

Product 1

HCID 23461463HCID 23461463, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a manner analogous to Example 10, from 0.96 g. p-toluoylglycine (m.p. 161°-162° C.) and 0.34 g. 2-cyanoaziridine in 10 ml. tetrahydrofuran, after the addition of 1.08 g. dicyclohexylcarbodiimide at 10°-15° C., stirring for 30 minutes at 10°-15° C. and for 2 hours at ambient temperature and after filtering off with suction 1.1 g. dicyclohexylurea (m.p. 228° C.) and evaporation of the filtrate in a vacuum, there is obtained the desired compound in crude form. This is dissolved in ethyl acetate, the solution is shaken up with a saturated aqueous solution of sodium bicarbonate and the organic phase is dried and evaporated. The evaporation residue is repeatedly triturated with diethyl ether to give 0.95 g. 1-(4-methylbenzamidoacetyl)-2-cyanoaziridine; m.p. 92°-94° C.

Workup

  1. filtrationafter filtering off with suction 1.1 g
  2. customdicyclohexylurea (m.p. 228° C.) and evaporation of the filtrate in a vacuum

Sources & evidence

ORD record
ord-ec6357942fdc4d9a8f511aecaa4b69fb
Source dataset
uspto-grants-1981_05
Patent number
US04267174

Reaction notes

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