4-Methoxyphenol → 2-((2-Hydroxy-3-((4-methoxyphenyl)diazenyl)-5-methylbenzyloxy)-carbonylamino)ethyl methacrylate

HRID 222454

Reaktionsgleichung

Reaktionsgleichung von HRID 222454
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([N:10]=[N:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:4]=1[OH:20].CCCCC(C([O-])=O)CC.CCCCC(C([O-])=O)CC.[Sn+2].[C:42]([O:47][CH2:48][CH2:49][N:50]=[C:51]=[O:52])(=[O:46])[C:43]([CH3:45])=[CH2:44].COC1C=CC(O)=CC=1>C1COCC1.C(OCC)C>[C:42]([O:47][CH2:48][CH2:49][NH:50][C:51]([O:1][CH2:2][C:3]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([N:10]=[N:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:4]=1[OH:20])=[O:52])(=[O:46])[C:43]([CH3:45])=[CH2:44]

Komponenten

7

Edukt 4

HCID 90154-MethoxyphenolHCID 93182-ethylhexanoic acid tin(II) saltHCID 354092-Isocyanatoethyl methacrylateHCID 1359935832-(Hydroxymethyl)-6-((4-methoxyphenyl)-diazenyl)-4-methylphenol

Produkt 1

HCID 1363932532-((2-Hydroxy-3-((4-methoxyphenyl)diazenyl)-5-methylbenzyloxy)-carbonylamino)ethyl methacrylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In a 500 ml 3-neck round bottom flask equipped with a magnetic stirrer and nitrogen inlet was dissolved 5.01 g (18.4 mmol) 2-(hydroxymethyl)-6-((4-methoxyphenyl)diazenyl)-4-methylphenol from Example 2 in 300 ml anhydrous THF. Stannous octoate (50 mg, Pfaltz & Bauer) was added followed by 2-isocyanatoethyl methacrylate (3.14 g, 20.2 mmol). MEHQ (100 mg) was added. The reaction mixture was stirred for 20 hr at 60° C. and then poured into 200 ml diethyl ether, and washed with 0.5 N HCl and water. The organic layer was dried with magnesium sulfate, filtered, and rotovapped to give the desired product which was recrystallized in ethanol to give 6.0 g (76%) of an orange solid. 1H NMR (CDCl3) delta: 13.22 (s, 1H, Ar—OH), 7.85 (m, 2H, Ar—H), 7.69 (s, 1H, Ar—H), 7.23 (s, 1H, Ar—HI), 7.03 (m, 2H, Ar—H), 6.09 (s, 1H, vinyl-H), 5.57 (s, 1H, vinyl-H), 5.24 (s, 2H, Ar—CH2), 5.02 (s, 1H, CONH), 4.24 (m, 2H, CH2OCO), 3.90 (s, 3H, Ar—OCH3), 3.53 (m, 2H, OCNHCH2), 2.38 (s, 3H, Ar—CH3), 1.92 (s, 3H, CH3—C═C).

Aufarbeitung

  1. customIn a 500 ml 3-neck round bottom flask equipped with a magnetic stirrer and nitrogen inlet
  2. washwashed with 0.5 N HCl and water
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-eee742eb482441429f94e75290417dbf
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207244B2

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