Dicyclohexylcarbodiimide → HCID 53674170, compound

HRID 2286571Notes

Reaction equation

HRID 2286571 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:21]=[CH:22][C:23]([OH:25])=O.[C:26]([CH:28]1[CH2:30][NH:29]1)#[N:27]>C(OCC)C>[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH:21]=[CH:22][C:23]([N:29]1[CH2:30][CH:28]1[C:26]#[N:27])=[O:25]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 10876Furylacrylic acidHCID 118115Aziridine-2-carbonitrile

Product 1

HCID 53674170HCID 53674170, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The same compound is obtained by introducing 2.1 g. dicyclohexylcarbodiimide, dissolved in 10 ml. diethyl ether, at 0° C. into a solution of 1.38 g. β-(2-furyl)acrylic acid and 0.68 g. 2-cyanoaziridine in 30 ml. diethyl ether, stirring for 2 hours at 0° C. and leaving to stand overnight at ambient temperature; after analogous purification on a silica gel column, there is obtained 0.9 g. of an oil which solidifies after standing for several days. After trituration with petroleum ether, the compound melts at 59°-61° C.

Workup

  1. customThe same compound is obtained
  2. additionby introducing 2.1 g
  3. customat 0° C.
  4. customleaving
  5. customafter analogous purification on a silica gel column
  6. customthere is obtained 0.9 g
  7. waitafter standing for several days

Sources & evidence

ORD record
ord-eafe9690bd524bb78f28532ef5f2c245
Source dataset
uspto-grants-1981_05
Patent number
US04267174

Reaction notes

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