Ammonia → 4-Carbamoylmethyl-2-(3,5-di-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-3-oxo-2H-1,4-benzothiazine

HRID 1439842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1439842
Cl.[C:2]([C:6]1[CH:7]=[C:8]([CH:27]=[C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:29]=1[OH:30])[CH:9]=[C:10]1[C:15](=[O:16])[N:14]([CH2:17][C:18]([O:20]CC)=O)[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=2[S:11]1)([CH3:5])([CH3:4])[CH3:3].[NH3:35]>CO>[C:18]([CH2:17][N:14]1[C:13]2[CH:23]=[CH:24][CH:25]=[CH:26][C:12]=2[S:11][C:10](=[CH:9][C:8]2[CH:27]=[C:28]([C:31]([CH3:33])([CH3:32])[CH3:34])[C:29]([OH:30])=[C:6]([C:2]([CH3:3])([CH3:5])[CH3:4])[CH:7]=2)[C:15]1=[O:16])(=[O:20])[NH2:35]

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 573062862-(3,5-di-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-4-ethoxycarbonylmethyl-3-oxo-2H-1,4-benzothiazine

Produkt 1

HCID 867493044-Carbamoylmethyl-2-(3,5-di-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-3-oxo-2H-1,4-benzothiazineAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

0.1N hydrochloric acid in methanol (3 ml) was added to a solution of 2-(3,5-di-tert.-butyl-4-hydroxybenzylidene)-3,4-dihydro-4-ethoxycarbonylmethyl-3-oxo-2H-1,4-benzothiazine (Compound No. 1-1, 0.4 g) in 17.85 N ammonia in methanol (15 ml). After the addition, the mixture was stirred for 4 days at 80° C. in a sealed tube and followed by concentration in vacuo. To the residue, dilute hydrochloric acid was added and the whole was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give 0.14 g (37.3%) of the titled compound.

Aufarbeitung

  1. additionAfter the addition
  2. concentrationfollowed by concentration in vacuo
  3. additionTo the residue, dilute hydrochloric acid was added
  4. extractionthe whole was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe oily residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-17e4048fb86340c8bcc37b1620311e75
Quelldatensatz
uspto-grants-1996_03
Patentnummer
US05496817

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