Thionyl Chloride → 2-(4-(Tert-butyl)phenyl)-4,4-dimethyl-4,5-dihydrooxazole

HRID 68461

Reaktionsgleichung

Reaktionsgleichung von HRID 68461
[C:1]([C:5]1[CH:18]=[CH:17][C:8]([C:9]([NH:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O>CCOCC>[C:1]([C:5]1[CH:18]=[CH:17][C:8]([C:9]2[O:14][CH2:13][C:12]([CH3:16])([CH3:15])[N:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 24386Thionyl ChlorideHCID 3200764-tert-Butyl-N-(2-hydroxy-1,1-dimethyl-ethyl)-benzamide

Produkt 1

HCID 3200722-(4-(Tert-butyl)phenyl)-4,4-dimethyl-4,5-dihydrooxazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

All of the 4-tert-butyl-N-(2-hydroxy-1,1-dimethyl-ethyl)-benzamide prepared above (174 mmol) was charged into a 500 mL round bottom flask fitted with a stir bar and septum. Established and maintained nitrogen atmosphere. Added 50 mL (685 mmol) of thionyl chloride dropwise over 20 min. Warmed the flask with a heat gun to dissolve some of the resin and initiate the reaction. The reaction mixture solidified. Warmed the flask with a heat gun to dissolve all the solids. Cooled to room temperature. Poured the reaction solution in a thin stream into 500 mL of stirred Et2O. A white precipitate formed. Collected the precipitate by filtration and washed thoroughly with Et2O. Dissolved the collected solids in 300 mL water and neutralized with 25% NaOH. Extracted the yellow aqueous solution with 2×200 mL Et2O. Washed the yellow extracts with 200 brine, dried over MgSO4, and removed the solvent on rotavap to obtain 28.50 g of the title compound as a waxy white solid. MS (ESI) 232 (M+H)+.

Aufarbeitung

  1. additionwas charged into a 500 mL round bottom flask
  2. customfitted with a stir bar
  3. temperatureEstablished and maintained nitrogen atmosphere
  4. temperatureWarmed the flask with a heat gun
  5. dissolutionto dissolve some of the resin
  6. customthe reaction
  7. temperatureWarmed the flask with a heat gun
  8. dissolutionto dissolve all the solids
  9. customA white precipitate formed
  10. customCollected the precipitate
  11. filtrationby filtration
  12. washwashed thoroughly with Et2O
  13. dissolutionDissolved the collected solids in 300 mL water
  14. extractionExtracted the yellow aqueous solution with 2×200 mL Et2O
  15. washWashed the yellow extracts with 200 brine
  16. dry with materialdried over MgSO4
  17. customremoved the solvent on rotavap

Quellen und Nachweise

ORD-Eintrag
ord-d07fab8a9fe345bf9d70c1926ec11b78
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822457B2

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