Hydrochloric Acid → 3-Ethoxy-2-hydroxy-5-(2-oxo-5,6-diphenyl-1,2,3,4-tetrahydropyrimidin-4-yl)benzonitrile

HRID 401044Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401044
[CH2:1]([O:3][C:4]1[C:5]([OH:14])=[C:6]([CH:9]=[C:10]([CH:12]=O)[CH:11]=1)[C:7]#[N:8])[CH3:2].[C:15]1([C:21](=O)[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[NH2:30][C:31]([NH2:33])=[O:32].Cl>CCO.CO.CCOC(C)=O>[CH2:1]([O:3][C:4]1[C:5]([OH:14])=[C:6]([CH:9]=[C:10]([CH:12]2[C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:33][C:31](=[O:32])[NH:30]2)[CH:11]=1)[C:7]#[N:8])[CH3:2]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 99482-PhenylacetophenoneHCID 866693323-Ethoxy-5-formyl-2-hydroxybenzonitrile

Produkt 1

HCID 513485173-Ethoxy-2-hydroxy-5-(2-oxo-5,6-diphenyl-1,2,3,4-tetrahydropyrimidin-4-yl)benzonitrileAusbeute 45,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 3-ethoxy-5-formyl-2-hydroxybenzonitrile (285 mg, 1.5 mmol), 1,2-diphenylethanone (320 mg, 1.6 mmol), and urea (270 mg, 4.5 mmol) in anhydrous EtOH (5 mL) was added concentrated HCl solution (0.5 mL). The reaction mixture was refluxed overnight. TLC (EtOAc:MeOH=10:1) showed 40% of the starting materials were consumed. The reaction mixture was concentrated, and purified by column chromatography (EtOAc:MeOH=40:1) and preparative HPLC to afford Compound 69 as a yellow solid (280 mg, yield: 45.7%). 1H NMR (DMSO-d6 400 MHz TMS): δ 10.30 (s, 1H), 8.70 (d, J=1.2 Hz, 1H), 7.47 (s, 1H), 7.20-7.27 (m, 5H), 7.16 (d, J=1.6 Hz, 1H), 6.98-7.06 (m, 4H), 6.80-6.82 (m, 2H), 5.14 (d, J=2.4 Hz, 1H), 4.00-4.10 (m, 2H), 1.33 (t, J=7.2 Hz, 3H); MS (ESI): m/z 412.1 [M+1]+.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed overnight
  2. customwere consumed
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by column chromatography (EtOAc:MeOH=40:1) and preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ccdb2436e00040a893e422b8239a7596
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741915B2

Notizen zur Reaktion

Wird geladen…