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

HRID 5826

Reaktionsgleichung

Reaktionsgleichung von HRID 5826
[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-95b2bc44ff6d4a949fc4fdaff92f4f93
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246929

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