Triethylamine → {2-[3-(1,1-Dimethylundecyl)ureido]-4-methoxy-6-tert-butylphenoxy}methoxymethane

HRID 1457574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1457574
C[C:2]([CH3:16])([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[C:3](O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.C([N:36]([CH2:39]C)CC)C.[NH2:41][C:42]1[CH:51]=[C:50]([O:52][CH3:53])[CH:49]=[C:48]([C:54]([CH3:57])([CH3:56])[CH3:55])[C:43]=1[O:44][CH2:45][O:46][CH3:47]>O.C1C=CC=CC=1>[CH3:16][C:2]([NH:36][C:39](=[O:24])[NH:41][C:42]1[CH:51]=[C:50]([O:52][CH3:53])[CH:49]=[C:48]([C:54]([CH3:57])([CH3:56])[CH3:55])[C:43]=1[O:44][CH2:45][O:46][CH3:47])([CH3:3])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 42657262,2-Dimethyldodecanoic acidHCID 18765846(2-Amino-4-methoxy-6-tert-butylphenoxy)methoxymethane

Produkt 1

HCID 22099452{2-[3-(1,1-Dimethylundecyl)ureido]-4-methoxy-6-tert-butylphenoxy}methoxymethane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 5 g of 2,2-dimethyllauric acid, 4.72 ml of diphenylphosphorylazide (DPPA), 3.36 ml of triethylamine and 80 ml of benzene was refluxed for one hour. After cooling, a mixed solution of 5.763 g of (2-amino-4-methoxy-6-tert-butylphenoxy)methoxymethane and 20 ml of benzene was added dropwise to the above mixture. The resulting mixture was stirred at room temperature for one hour and then under reflux for 10 hours. Water was added to the reaction mixture, and the reaction mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1) and the product was recrystallized from hexane to give 2.89 g of {2-[3-(1,1-dimethylundecyl)ureido]-4-methoxy-6-tert-butylphenoxy}methoxymethane (melting point: 83°-85° C.).

Aufarbeitung

  1. temperaturewas refluxed for one hour
  2. temperatureAfter cooling
  3. temperatureunder reflux for 10 hours
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe extract was washed
  6. customdried
  7. customthe solvent was removed under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=4:1)
  9. customthe product was recrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-18e8b5c3d7bc4257a1aa16d682bbc4bf
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05849732

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