Ethanol → Teniloxazine

HRID 1415402Notes

Reaction equation

HRID 1415402 reaction equation
[C:1]1([CH2:6][C:7]2[CH:17]=[CH:16][CH:15]=[CH:14][C:8]=2[O:9][CH2:10][CH:11]2[O:13][CH2:12]2)[S:5][CH:4]=[CH:3][CH:2]=1.S(O)([O:21][CH2:22][CH2:23][NH2:24])(=O)=O.[OH-:26].[Na+].C([OH:30])C>O>[C:11]([OH:13])(=[O:30])/[CH:12]=[CH:23]\[C:22]([OH:21])=[O:26].[C:1]1([CH2:6][C:7]2[CH:17]=[CH:16][CH:15]=[CH:14][C:8]=2[O:9][CH2:10][CH:11]2[O:21][CH2:22][CH2:23][NH:24][CH2:12]2)[S:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 70223Aminoethyl sulfateHCID 132774152-({2-[(Thiophen-2-yl)methyl]phenoxy}methyl)oxirane

Product 1

HCID 6438129Teniloxazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 19 g of 1-[2-(2-thenyl)phenoxy]-2,3-epoxypropane, 65 g of 2-aminoethyl hydrogen sulfate, 40 g of sodium hydroxide, 350 ml of ethanol and 200 ml of water was heated under reflux with stirring for 23 hours. Most of the ethanol was distilled off, and the residue was extracted with two 400 ml portions of ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. To the residue was added a solution of maleic acid in ethanol. The precipitated crystals were purified in the same manner as in Example 1 to give 2-[2-(2-thenyl)phenoxymethyl]morpholine maleate as colorless crystals, melting at 155°-156° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. distillationMost of the ethanol was distilled off
  4. extractionthe residue was extracted with two 400 ml portions of ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe ethyl acetate was distilled off under reduced pressure
  8. additionTo the residue was added a solution of maleic acid in ethanol
  9. customThe precipitated crystals were purified in the same manner as in Example 1

Sources & evidence

ORD record
ord-9c3b7e4649d3476ca24bd96d8b593411
Source dataset
uspto-grants-1977_01
Patent number
US04005084

Reaction notes

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