Hydrochloric Acid → Pentoxazone

HRID 2289008

Reaktionsgleichung

Reaktionsgleichung von HRID 2289008
[Cl:1][C:2]1[C:7]([O:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:6][C:5]([NH:14][C:15](=[O:19])[O:16][CH2:17][CH3:18])=[C:4]([F:20])[CH:3]=1.[OH:21]C(C(C)=C)C(OCC)=O.Cl.[C:32]1([CH3:38])C=CC=C[CH:33]=1>>[Cl:1][C:2]1[C:7]([O:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13]2)=[CH:6][C:5]([N:14]2[C:18](=[O:21])[C:17](=[C:32]([CH3:38])[CH3:33])[O:16][C:15]2=[O:19])=[C:4]([F:20])[CH:3]=1

Komponenten

5

Edukt 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 108555893-Butenoic acid, 2-hydroxy-3-methyl-, ethyl esterHCID 11033971N-[4-Chloro-5-(cyclopentyloxy)-2-fluorophenyl]carbamic acid ethyl ester

Produkt 1

HCID 11714234PentoxazoneAusbeute 50,9 %

Versuchsvorschrift

Ethyl N-(4-chloro-5-cyclopentyloxy-2-fluorophenyl)carbamate (3.01 g, 10 mmol) and ethyl 2-hydroxy-3-methyl-3-butenoate (4.32 g, 30.0 mmol) were introduced into a flask (25 cc) equipped with a distillation unit, and the reaction was conducted at 215° C. for 16.5 hours. After the reaction solution was cooled to room temperature, toluene (20 mL) was added, and then the reaction solution was washed with water (20 mL), then 1N sodium hydroxide (20 mL) and 1N hydrochloric acid (20 mL). The organic layer was dried over magnesium sulfate. After the drying agent was filtered off, the filtrate was concentrated under reduced pressure. To the resulting oily crude product, methanol (3.5 mL) acidified with hydrochloric acid was added to form a homogeneous solution. Then, 6N hydrochloric acid (0.4 mL) was further added, and the solution was left to stand at room temperature. The precipitated crystals were collected by filtration, then washed with a 10:1 mixed solvent consisting of methanol and 6N hydrochloric acid and dried to obtain 3-(4-chloro-5-cyclopentyloxy-2-fluorophenyl)-5-isopropylidene-1,3-oxazolidine-2,4-dione (1.80 g, yield 50.9%).

Aufarbeitung

  1. customequipped with a distillation unit
  2. washthe reaction solution was washed with water (20 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationAfter the drying agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionwas added
  7. customto form a homogeneous solution
  8. waitthe solution was left
  9. customto stand at room temperature
  10. filtrationThe precipitated crystals were collected by filtration
  11. washwashed with a 10:1 mixed solvent
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-9e852a79dcf244eb940c3179a8a08cfc
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06090946

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