Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1763223Notes

Reaction equation

HRID 1763223 reaction equation
C(O)[C@@H](O)C(O)=[O:4].NC=CC1C=CC=CC=1.[CH:17]1([N:23]=[C:24]=[N:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C(#N)C>[CH:26]1([NH:25][C:24]([NH:23][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)=[O:4])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 155076Ethenamine, 2-phenyl-HCID 439194(2R)-2,3-Dihydroxypropanoic acid

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution (cooled to 0° C) of 5.3 g (0.05 mole) D-glyceric acid in 150 ml of acetonitrile, there was added 8.9 g (0,075 mole) β - aminostyrene and 10.3 g (0.05 mole) N.N' - dicyclohexylcarbodiimide. A precipitate of N.N' - dicyclohexylurea is formed immediately, but the reaction was allowed to proceed for 15 hours at room temperature. After filtration and removal of the acetonitrile by distillation under reduced pressure, the residue was taken up in ethyl acetate and extracted with HCl, bicarbonate and water. After drying and removal of the solvent the residue was crystallized from chloroform, yielding 7.5 g (73%), m.p. 135°-136° C.

Sources & evidence

ORD record
ord-7c70c06f35834dd4a7cc9fcf76960afb
Source dataset
uspto-grants-1978_09
Patent number
US04111863

Reaction notes

Loading…