Ethanol → HCID 86735474, compound

HRID 616307Notes

Reaction equation

HRID 616307 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH2:21][CH:22]3[O:24]C3)[S:16](=[O:18])(=[O:17])[CH2:15][CH2:14][CH2:13][S:12]2(=[O:20])=[O:19])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:25](O)C.C(Cl)(Cl)Cl.[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34]>CC(C)=O>[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[CH3:25][CH:15]1[CH2:14][CH2:13][S:12](=[O:19])(=[O:20])[C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)([CH2:21][CH2:22][OH:24])[S:16]1(=[O:17])=[O:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 971Oxalic AcidHCID 6212ChloroformHCID 22758373HCID 22758373, compound

Product 1

HCID 86735474HCID 86735474, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3.76 g of 2-(3,4-dimethoxyphenyl)-2-(2,3-epoxypropyl)-m-dithiane-1,1,3,3-tetraoxide are heated at reflux for 18 hours under argon with 50 ml of ethanol, 30 ml of chloroform and 1.95 g of N-methyl-homovetratrylamine. After evaporation of the solvent, the residue is chromatographed on silica gel with chloroform/ethanol (98:2). The oil obtained is dissolved in acetone and treated with an equivalent amount of anhydrous oxalic acid. The precipitate is filtered off and recrystallized from methanol/acetone. The racemic α- (3,4-dimethoxyphenethyl)-methylamino!-methyl-2-(3,4-dimethoxyphenyl)-m-dithiane-2-ethanol-1,1,3,3-tetraoxide oxalate (1:1) obtained crystallizes with 1 mol of acetone and melts at 162°-164° C.

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue is chromatographed on silica gel with chloroform/ethanol (98:2)
  3. customThe oil obtained
  4. filtrationThe precipitate is filtered off
  5. customrecrystallized from methanol/acetone

Sources & evidence

ORD record
ord-f9b1553e33ab4ac0a3f094d2e70fcabc
Source dataset
uspto-grants-1978_02
Patent number
US04073797

Reaction notes

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