Sodium Hydroxide → 1H,2H,4H-thieno(3,2-d)(1,3)oxazine-2,4-dione

HRID 67475

Reaktionsgleichung

Reaktionsgleichung von HRID 67475
Cl.[NH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([O:10][CH3:11])=[O:9].[OH-:12].[Na+]>C(O)CCC>[NH:2]1[C:3]2[CH:7]=[CH:6][S:5][C:4]=2[C:8](=[O:9])[O:10][C:11]1=[O:12]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 12517407Methyl 3-amino-2-thiophenecarboxylate hydrochloride

Produkt 1

HCID 27775521H,2H,4H-thieno(3,2-d)(1,3)oxazine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 175 g (0.93 mol) of methyl 3-amino-2-thiophenecarboxylate hydrochloride, 1.8 liters of n-butanol and 77 g of sodium hydroxide is heated to boiling under reflux for 30 minutes. After concentration of the resulting suspension on a rotary evaporator, the mixture of sodium 3-amino-2-thiophenecarboxylate and sodium chloride is used directly in the next step. For this purpose, the mixture is treated with 800 ml of water, 280 ml of concentrated hydrochloric acid and 230 ml of tetrahydrofuran. Phosgene is conducted through this mixture at 15°-25° C. for 2.5 hours and then air is conducted through for 15 minutes. The separated solid material is filtered off under suction, washed with water and dried. There is obtained 2H-thieno[3,2-d][1,3]-oxazine-2,4(1H)-dione of melting point 220°-221° C.

Aufarbeitung

  1. temperatureis heated
  2. temperatureunder reflux for 30 minutes
  3. customAfter concentration of the resulting suspension on a rotary evaporator
  4. additionthe mixture of sodium 3-amino-2-thiophenecarboxylate and sodium chloride
  5. additionFor this purpose, the mixture is treated with 800 ml of water, 280 ml of concentrated hydrochloric acid and 230 ml of tetrahydrofuran
  6. customis conducted through for 15 minutes
  7. filtrationThe separated solid material is filtered off under suction
  8. washwashed with water
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-013ecfba21b34916a19e3f26f4396382
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04346034

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