Oxalic Acid → 4-(N-allyl-N-methylaminoacetyl)-2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine oxalate

HRID 1198438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1198438
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][N:12]([C:14](=[O:18])[CH2:15][NH:16][CH3:17])[C:11]3[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=3[S:9]2)=[CH:4][CH:3]=1.[CH2:23](Br)[CH:24]=[CH2:25].C(=O)([O-])[O-].[K+].[K+].[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35]>CCOCC.O.CN(C)C=O>[C:33]([OH:38])(=[O:37])[C:34]([OH:36])=[O:35].[CH2:23]([N:16]([CH2:15][C:14]([N:12]1[C:11]2[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=2[S:9][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:13]1)=[O:18])[CH3:17])[CH:24]=[CH2:25]

Komponenten

8

Edukt 4

HCID 971Oxalic AcidHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 189844352-(4-chlorophenyl)-4-(N-methylaminoacetyl)-3,4-dihydro-2H-1,4-benzothiazine

Produkt 1

HCID 189844334-(N-allyl-N-methylaminoacetyl)-2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine oxalate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-chlorophenyl)-4-(N-methylaminoacetyl)-3,4-dihydro-2H 1,4-benzothiazine (1.80 g), allyl bromide (0.52 ml), potassium carbonate (2.25 g) and dimethylformamide (20 ml) is stirred at room temperature for 3.5 hours. The reaction mixture is poured into water, and the mixture is extracted with ethyl acetate. After the solvent is distilled off, the residue is purified by silica gel column chromatography (solvent, chloroform: methanol=40:1). The caramel thus obtained is dissolved in ether and thereto is added 1.1 equivalent of oxalic acid. The resulting precipitate is washed with ether and dried to give 4-(N-allyl-N-methylaminoacetyl)-2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine oxalate as powder.

Aufarbeitung

  1. extractionthe mixture is extracted with ethyl acetate
  2. distillationAfter the solvent is distilled off
  3. customthe residue is purified by silica gel column chromatography (solvent, chloroform: methanol=40:1)
  4. customThe caramel thus obtained
  5. washThe resulting precipitate is washed with ether
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-0c52273dcace4b798b3160f88dfa282f
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05281592

Notizen zur Reaktion

Wird geladen…