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

HRID 5826

Reaction equation

HRID 5826 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-95b2bc44ff6d4a949fc4fdaff92f4f93
Source dataset
uspto-grants-1993_09
Patent number
US05246929

Linked notes

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