4-Methoxybenzoic Acid → N,N'-Dicyclohexylurea

HRID 2286563Notes

Reaction equation

HRID 2286563 reaction equation
C[O:2]C1C=CC(C(O)=O)=CC=1.C(C1CN1)#N.[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>O1CCOCC1>[CH:26]1([NH:25][C:24]([NH:23][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)=[O:2])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 74784-Methoxybenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 118115Aziridine-2-carbonitrile

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

1.52 g. p-Methoxybenzoic acid is dissolved in 20 ml. dioxan and mixed at 10° C. with a solution of 0.68 g. 2-cyanoaziridine in 3 ml. dioxan. A solution of 2.06 g. dicyclohexylcarbodiimide in 4 ml. dioxan is added thereto and the reaction mixture is stirred for 2 hours at 8°-10° C. The crystals formed (2 g. 1,3-dicyclohexylurea; m.p. 225°-230° C.) are filtered off with suction and the filtrate is evaporated in a vacuum. The semi-solid evaporation residue (3.88 g.) is triturated with 3 ml. anhydrous diethyl ether, the crystals obtained (0.6 g.) are filtered off with suction, the filtrate is evaporated in a vacuum and the evaporation residue (2.45 g.) is again triturated with 3-4 ml. diethyl ether and filtered with suction to give 0.59 g. 1-p-methoxybenzoyl-2-cyanoaziridine; m.p. 81°-83° C. A further 0.18 g. of the desired product are obtained from the mother liquor by again evaporating and triturating the evaporation residue with diethyl ether.

Sources & evidence

ORD record
ord-9ae4e5ec3bcd4d0fad8bb27f6097f985
Source dataset
uspto-grants-1981_05
Patent number
US04267174

Reaction notes

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