Dicyclohexylcarbodiimide → 4-Amidino-2-benzoylphenyl 4-benzyloxybenzoate

HRID 1981441Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1981441
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:38]1[CH:43]=[CH:42][C:41]([C:44](=[NH:46])[NH2:45])=[CH:40][C:39]=1[C:47](=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)(=O)=O>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][C:38]2[CH:43]=[CH:42][C:41]([C:44](=[NH:45])[NH2:46])=[CH:40][C:39]=2[C:47](=[O:54])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:14])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 738804-(Benzyloxy)benzoic acidHCID 540991824-Amidino-2-benzoylphenol methanesulfonate

Produkt 1

HCID 131784714-Amidino-2-benzoylphenyl 4-benzyloxybenzoateAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a mixture of 3.4 g of 4-benzyloxybenzoic acid and 50 ml of dried pyridine, while being cooled in ice, was added 3.7 g of DCC. After having been stirred for 30 minutes, the mixture was admixed with 5.0 g of 4-amidino-2-benzoylphenol methanesulfonate and stirred overnight at room temperature. The reaction mixture was freed from the insolubles by filtration and mixed with ethyl ether. The precipitated insoluble substance was recrystallized from a methanol-ethyl ether mixture to obtain 5.2 g of colorless crystals of 4-amidino-2-benzoylphenyl 4-benzyloxybenzoate methanesulfonate.

Aufarbeitung

  1. temperaturewhile being cooled in ice
  2. stirringstirred overnight at room temperature
  3. filtrationThe reaction mixture was freed from the insolubles by filtration
  4. additionmixed with ethyl ether
  5. customThe precipitated insoluble substance was recrystallized from a methanol-ethyl ether mixture

Quellen und Nachweise

ORD-Eintrag
ord-7bfdf65445eb4e8aac747027ddda88ff
Quelldatensatz
uspto-grants-1985_04
Patentnummer
US04514416

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