Retinoyl chloride → Retinamide

HRID 429587

Reaktionsgleichung

Reaktionsgleichung von HRID 429587
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]/[C:18](Cl)=[O:19].O.[NH3:24]>O1CCCC1>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]/[C:18]([NH2:24])=[O:19]

Komponenten

4

Edukt 2

HCID 10881705Retinoyl chlorideHCID 12896473Azane;hydrate

Produkt 1

HCID 5370221RetinamideAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

10 g (0.031 mole) of retinoic acid chloride as prepared according to the procedure described in Example 2 was added to the mixture of 300 ml of ammonia water (35%) and 100 ml of tetrahydrofuran and then stirred at room temperature for 20 hours. The reaction solution was distilled under reduced pressure and then concentrated. The residue was extracted with methylene chloride. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, filtered and then distilled under reduced pressure to obtain 9.43 g (Yield 99%) of the desired retinamide.

Aufarbeitung

  1. distillationThe reaction solution was distilled under reduced pressure
  2. concentrationconcentrated
  3. extractionThe residue was extracted with methylene chloride
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. distillationdistilled under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6572553c177743bea7be0af2dd8a8236
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06316644B1

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