Dicyclohexylcarbodiimide → HCID 23461517, compound

HRID 2286566Notes

Reaction equation

HRID 2286566 reaction equation
[C:1]([NH:4][CH2:5][C:6]([OH:8])=O)(=[O:3])[CH3:2].[C:9]([CH:11]1[CH2:13][NH:12]1)#[N:10].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[C:1]([NH:4][CH2:5][C:6]([N:12]1[CH2:13][CH:11]1[C:9]#[N:10])=[O:8])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 10972AcetylglycineHCID 118115Aziridine-2-carbonitrile

Product 1

HCID 23461517HCID 23461517, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.85 g. N-Acetylglycine, 3.4 g. 2-cyanoaziridine and 10.8 g. dicyclohexylcarbodiimide are stirred in 60 ml. tetrahydrofuran for 2 hours at ambient temperature. The precipitated dicyclohexylurea is filtered off, the filtrate is evaporated and the residue is stirred with diethyl ether, 5.2 g. of crude product thus being obtained. This water-soluble product is recrystallized from methanolic diethyl ether to give 1-(N-acetylglycyl)-2-cyanoaziridine, which melts at 102°-104° C.

Workup

  1. filtrationThe precipitated dicyclohexylurea is filtered off
  2. customthe filtrate is evaporated
  3. customof crude product thus being obtained
  4. customThis water-soluble product is recrystallized from methanolic diethyl ether

Sources & evidence

ORD record
ord-5b73be527205431cad1424701d5672c8
Source dataset
uspto-grants-1981_05
Patent number
US04267174

Reaction notes

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