Ethanol → Teniloxazine

HRID 1415403Notes

Reaction equation

HRID 1415403 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+].C1(C)C=CC=CC=1.C([OH:37])C>O>[C:11]([OH:13])(=[O:37])/[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

7

Reactant 5

HCID 702EthanolHCID 1140TolueneHCID 14798Sodium Hydroxide2×HCID 70223Aminoethyl sulfateHCID 132774152-({2-[(Thiophen-2-yl)methyl]phenoxy}methyl)oxirane

Product 1

HCID 6438129Teniloxazine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A solution of 22 g of 1-[2-(2-thenyl)phenoxy]-2,3-epoxypropane in 200 ml of ethanol was added to a mixture of 56 g of 2-aminoethyl hydrogen sulfate, 20 g of sodium hydroxide and 20 ml of water with stirring, and the stirring was continued for 4 hours at room temperature. To the mixture containing the intermediate, 2-[3-(2-hydroxy-3-[2-(2-thenyl)phenoxy]propylamino]-ethyl hydrogen sulfate, was added a solution of 40 g of sodium hydroxide in 40 ml of water, and the resulting mixture was stirred for 18 hours on a water bath. To the reaction mixture were added 500 ml of water and 700 ml of toluene. The toluene layer was washed with water and dried over anhydrous sodium sulfate, and the toluene was distilled off under reduced pressure. The oily residue was treated 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. stirringthe resulting mixture was stirred for 18 hours on a water bath
  2. washThe toluene layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe toluene was distilled off under reduced pressure
  5. additionThe oily residue was treated in the same manner as in Example 1

Sources & evidence

ORD record
ord-deedbd5090d54afc965c1a988f2985ba
Source dataset
uspto-grants-1977_01
Patent number
US04005084

Reaction notes

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