StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Hydrochloric Acid → 2-Amino-2-(6-(4-phenoxyphenoxy)naphthalen-2-yl)propane-1,3-diol

HRID 1036506
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1036506
CC1(C)[O:7][CH2:6][C:5]([NH2:32])([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([O:18][C:19]4[CH:24]=[CH:23][C:22]([O:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)=[CH:21][CH:20]=4)[CH:14]=3)[CH:9]=2)[CH2:4][O:3]1.CO.Cl.O>>[NH2:32][C:5]([C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)=[CH:21][CH:20]=3)[CH:14]=2)[CH:9]=1)([CH2:4][OH:3])[CH2:6][OH:7]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 674244522,2-Dimethyl-5-(6-(4-phenoxyphenoxy)naphthalen-2-yl)-1,3-dioxan-5-amine

Produkt 1

HCID 674236932-Amino-2-(6-(4-phenoxyphenoxy)naphthalen-2-yl)propane-1,3-diolAusbeute 78,2 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

2,2-Dimethyl-5-[6-(4-phenoxy-phenoxy)-naphthalen-2-yl]-1,3-dioxinan-5-ylamine (0.1241 g, 0.0002811 mol) was dissolved in methanol (3 mL, 0.07 mol) and a solution of 1 M of hydrogen chloride in water (5 mL, 0.005 mol) in a 40 mL reaction vial equipped with a magnetic stir bar. The vial was capped and heated at 90° C. overnight. TLC analysis showed that the reaction was complete. The reaction mixture was concentrated to dryness under reduced pressure. The resulting solid was dissolved in methylene chloride (5 mL) and washed with water then aqueous sodium carbonate. The combined organic layer was dried over magnesium sulfate, then concentrated under vacuum and purified by HPLC to give 88.3 mg of the title compound (78% yield). MS: m/z=424.45 [M+Na+]. 1H NMR (DMSO-d6) δ: 8.00 (s, 1H), 7.93 (d, J=8.7 Hz, 1H), 7.80 (d, J=8.7 Hz, 1H), 7.62-7.68 (m, 1H), 7.39-7.44 (m, 2H), 7.35-7.39 (m, 2H), 7.30 (dd, J=8.9, 2.5 Hz, 1H), 7.00-7.17 (m, 6H), 3.73 (d, J=3.8 Hz, 4H)

Aufarbeitung

  1. customvial equipped with a magnetic stir bar
  2. customThe vial was capped
  3. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  4. dissolutionThe resulting solid was dissolved in methylene chloride (5 mL)
  5. washwashed with water
  6. dry with materialThe combined organic layer was dried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. custompurified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b85d7aa72b134e81a8c944f4a08a05ce
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546359B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion