Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 2286570Notes

Reaction equation

HRID 2286570 reaction equation
[CH:1]1([N:7]=[C:8]=[N:9][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(CC(O)=O)(=[O:18])N.C(C1CN1)#N>O1CCCC1>[C:8]([NH:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([NH:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)=[O:18]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 753673-Amino-3-Oxopropanoic AcidHCID 118115Aziridine-2-carbonitrile

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2.15 g. Dicyclohexylcarbodiimide are introduced portionwise at 0° to 5° C. into a suspension of 1.03 g. carbamoylacetic acid and 0.68 g. 2-cyanoaziridine in 18 ml. tetrahydrofuran. The reaction mixture is stirred for 1 hour at 0° C. and then for 2 hours at ambient temperature. It is then filtered with suction and the solid material is washed with tetrahydrofuran and diethyl ether into the filtrate, 2.2 g. dicyclohexylurea (m.p. 226°-228° C.) being obtained. The filtrate is evaporated in a vacuum and the evaporation residue is triturated with ether to give 1.3 g. 1-carbamoylacetyl-2-cyanoaziridine; m.p. 115°-119° C.

Workup

  1. waitfor 2 hours at ambient temperature
  2. filtrationIt is then filtered with suction
  3. washthe solid material is washed with tetrahydrofuran and diethyl ether into the filtrate, 2.2 g

Sources & evidence

ORD record
ord-71adc97e9e564a7ca15bf66a3492acaa
Source dataset
uspto-grants-1981_05
Patent number
US04267174

Reaction notes

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