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Dichloromethane → HCID 15887790, Verbindung

HRID 1637886
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1637886
CC[N:3]([CH2:6][CH3:7])[CH2:4][CH3:5].C1CCC(N=[C:15]=[N:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)CC1.[CH:23]1[CH:24]=[CH:25]C2N(O)N=N[C:27]=2[CH:28]=1.[C:33]([NH:36][C:37]1[CH:42]=[CH:41][C:40](/[CH:43]=[CH:44]/[C:45]([OH:47])=O)=[CH:39][CH:38]=1)(=[O:35])[CH3:34].[CH2:48](Cl)Cl>C(Cl)Cl.CO>[O:47]=[C:45]([N:3]1[CH2:4][CH2:5][C:48]2[C:18]3[C:17](=[CH:22][CH:21]=[CH:20][CH:19]=3)[NH:16][C:15]=2[CH:6]1[C:7]1[CH:25]=[CH:24][CH:23]=[CH:28][CH:27]=1)/[CH:44]=[CH:43]/[C:40]1[CH:39]=[CH:38][C:37]([NH:36][C:33](=[O:35])[CH3:34])=[CH:42][CH:41]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 53571554-Acetamidocinnamic acid

Produkt 1

HCID 15887790HCID 15887790, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

To a solution of Intermediate 1 (0.2 g, 0.81 mmol) in 40 mL of DCM were added Et3N (0.13 mL, 1.1 equiv.), DCC (0.18 g, 1.1 equiv.), HOBT (0.12 g, 1.1 equiv.) and (E)-3-(4-acetylaminophenyl)acrylic acid (0.18 g, 1.1 equiv.). After 24 hours of stirring at rt the reaction was judged to be completed by tlc monitoring (SiO2, DCM:MeOH 95:5) and was quenched with 150 mL of water. A white solid precipitated out and was filtered off. The filtrate was extracted with DCM, washed with brine (5 mL), dried over MgSO4 and concentrated in vacuo. Flash chromatography on a 2.5×25 cm2 column of silica gel using DCM:MeOH (98:2) as eluting solvent and removal of the solvent in vacuo gave the title compound (0.18 g, 51%) as yellow crystals after recrystallization from 2-propanol:pentane. MP: 177-180° C.

Aufarbeitung

  1. customwas quenched with 150 mL of water
  2. customA white solid precipitated out and
  3. filtrationwas filtered off
  4. extractionThe filtrate was extracted with DCM
  5. washwashed with brine (5 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. washas eluting
  9. customsolvent and removal of the solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bac2f58456a14119b44d5006b24e913d
Quelldatensatz
uspto-grants-2000_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06043252

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