Water → HCID 21498578, compound

HRID 1578933Notes

Reaction equation

HRID 1578933 reaction equation
[OH2:1].[CH2:2]1[O:4][CH2:3]1.[NH:5]1[CH2:10][CH2:9][NH:8][CH:7]2[CH2:11][S:12](=[O:15])(=[O:14])[CH2:13][CH:6]12.[C:16]1([CH3:22])C=CC=CC=1>>[N:5]1([CH2:3][CH2:2][OH:4])[CH2:10][CH2:9][N:8]([CH2:22][CH2:16][OH:1])[CH:7]2[CH2:11][S:12](=[O:15])(=[O:14])[CH2:13][CH:6]12

Participants

5

Reactant 4

HCID 962Water3×HCID 1140TolueneHCID 6354Ethylene OxideHCID 16449569Octahydro-6H-6lambda~6~-thieno[3,4-b]pyrazine-6,6-dione

Product 1

HCID 21498578HCID 21498578, compound

Procedure

This example illustrates the preparation of a typical diol of this invention using a reactive, watersoluble epoxide. (Water soluble epoxides have at most four carbon atoms). 2.5 ml. (0.05 mole) of ethylene oxide was condensed into a reaction flask and dissolved in 5 ml. of water. To this solution was added gradually at room temperature, a solution of 3.5 g. (0.02 mole) in 5 ml. of water of 1,2,3,4,4a,5,7,7a-octahydrothieno[3,4-b]pyrazine 6,6-dioxide, the diamine of Example 1. After the reaction was complete, the reaction mixture was allowed to cool to room temperature and the waterr and excess epoxide were removed under vacuum, leaving a white solid. Trituration with toluene gave a product, 1,2,3,4,4a,5,7,7a-octahydrothieno[3,4-b]pyrazine 1,4-diethanol 6,6-dioxide, M.P. 145°-147°C. IR spectrum showed bands at 3300 cm-1, broad (OH) at 1285 cm-1 and 1125 cm-1 (SO2) and at 1010 cm-1 (CO).

Workup

  1. customcondensed into a reaction flask
  2. dissolutiondissolved in 5 ml
  3. additionTo this solution was added gradually at room temperature
  4. customthe waterr and excess epoxide were removed under vacuum
  5. customleaving a white solid

Sources & evidence

ORD record
ord-afde315360f545919f46a36f28e08bf2
Source dataset
uspto-grants-1976_02
Patent number
US03940396

Reaction notes

Loading…