Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 537720

Reaktionsgleichung

Reaktionsgleichung von HRID 537720
C[O:2]C(=O)CCCCC(O)=O.[CH2:12]1[CH2:17][CH2:16][CH:15]([N:18]=[C:19]=[N:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:14][CH2:13]1.ON1C(=O)CCC1=O>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:19]([NH:18][CH:15]1[CH2:14][CH2:13][CH2:12][CH2:17][CH2:16]1)([NH:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:2]

Komponenten

6

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 12328monoMethyl adipateHCID 80170N-Hydroxysuccinimide

Produkt 1

HCID 4277N,N'-Dicyclohexylurea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Step 1, Compound 4: Adipic acid monomethyl ester is treated with one molar equivalent of DCC, DMAP and N-hydroxysuccinimide in DMF for 30 min. To this a molar equivalent of the compound obtained from Step 3a (Example 1) is added and stirred at ambient temperature for 8 h. Dicylcohexylurea formed during the course of the reaction is filtered off and the product is extracted into ethyl acetate, washed with sodium bicarbonate solution followed by standard workup. The methyl ester thus obtained is treated with LiOH in THF/water to obtain compound 4.

Quellen und Nachweise

ORD-Eintrag
ord-f1cf80c97c0745ac99ef57d6f3b6c1ab
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865677B2

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