1,2-Dimethoxyethane → 2-[4-(Hexadecylamino)phenyl]oxazoline

HRID 1980189

Reaktionsgleichung

Reaktionsgleichung von HRID 1980189
Br.Br[CH2:3][CH2:4][NH2:5].C(COC)OC.Cl.[CH2:13]([NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[CH2:13]([NH:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]2[O:35][CH2:3][CH2:4][N:5]=2)=[CH:32][CH:31]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28]

Komponenten

6

Edukt 3

HCID 80711,2-Dimethoxyethane2×HCID 27742172-Bromoethylamine hydrobromideHCID 132553224-Hexadecylaminobenzoyl chloride hydrochloride

Produkt 1

HCID 204373702-[4-(Hexadecylamino)phenyl]oxazoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a slurry of 15 g. of 2-bromoethylamine hydrobromide in 150 ml. of glyme was added simultaneously solutions of 31 g. of 4-(hexadecylamino)benzoyl chloride hydrochloride in 60 ml. of glyme and 50 cc. of triethylamine (dropwise). Upon addition of 0.5 g. of 4-dimethylaminopyridine the "solution" was stirred at room temperature overnight. The solution was refluxed for one hour and filtered. The solid was oven dried and portitioned between CH2Cl and water. The layers were separated and the organic phase dried over MgSO4. The organic layer was concentrated to about 100 ml. and 4-(hexadecylamino)benzoyl chloride hydrochloride diluted with an equal volume of hexane. The combined product (4.15 g.) was preabsorbed on 40 g. of silica III and placed on a column of silica III (800 g.). Fractions were collected by U.V. (CH2Cl2 -EtOH 97-3) and samples with the same TLC combined giving 3.8 g. after recrystallization from cyclohexane. A 210 mg. sample was recrystallized from acetonitrile and CH2Cl2 /hexane giving 149 mg., m.p. 123°-125° C.

Aufarbeitung

  1. additionUpon addition of 0.5 g
  2. temperatureThe solution was refluxed for one hour
  3. filtrationfiltered
  4. customdried
  5. customThe layers were separated
  6. dry with materialthe organic phase dried over MgSO4
  7. concentrationThe organic layer was concentrated to about 100 ml
  8. additionand 4-(hexadecylamino)benzoyl chloride hydrochloride diluted with an equal volume of hexane
  9. customThe combined product (4.15 g.) was preabsorbed on 40 g
  10. customFractions were collected by U.V
  11. custom(CH2Cl2 -EtOH 97-3) and samples with the same TLC combined giving 3.8 g
  12. customafter recrystallization from cyclohexane
  13. customsample was recrystallized from acetonitrile and CH2Cl2 /hexane giving 149 mg

Quellen und Nachweise

ORD-Eintrag
ord-1749f76670204218b3036bfac611332e
Quelldatensatz
uspto-grants-1984_11
Patentnummer
US04485105

Verknüpfte Notizen

Wird geladen…