4-(3-Chloropropyl)morpholine → 4,4'-[1,3,4-Thiadiazole-2,5-diylbis(sulfanediylpropane-3,1-diyl)]bis(morpholine)

HRID 616420Notes

Reaction equation

HRID 616420 reaction equation
[K].[K].[SH:3][C:4]1[S:5][C:6]([SH:9])=[N:7][N:8]=1.Cl[CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>O>[N:14]1([CH2:13][CH2:12][CH2:11][S:3][C:4]2[S:5][C:6]([S:9][CH2:11][CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:7][N:8]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 958344-(3-Chloropropyl)morpholineHCID 178527977HCID 178527977, compound

Product 1

HCID 203702304,4'-[1,3,4-Thiadiazole-2,5-diylbis(sulfanediylpropane-3,1-diyl)]bis(morpholine)

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 17.0 grams (0.075 mole) of 2,5-dimercapto-1,3,4-thiadiazole dipotassium salt and 24.5 grams (0.150 mole) of 4-(3-chloropropyl)-morpholine in 170 ml of water was heated under reflux with stirring for two hours. The mixture was then cooled to between 28 and 30° C and extracted with benzene. The benzene extract was washed with a saturated sodium chloride solution and dried over anhydrous sodium carbonate. After removal of the drying agent by filtration, the solution was evaporated to dryness, leaving the 2,5-bis(3-(4-morpholinyl)propylthio)-1,3,4-thiadiazole as a pale yellow oil. The product was recrystallized from methylcyclohexane to give white crystals with a melting point of 65.5°-66° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureThe mixture was then cooled to between 28 and 30° C
  4. extractionextracted with benzene
  5. extractionThe benzene extract
  6. washwas washed with a saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium carbonate
  8. customAfter removal of the drying agent
  9. filtrationby filtration
  10. customthe solution was evaporated to dryness

Sources & evidence

ORD record
ord-7c5f94cf5ce54615acff29edb14e6881
Source dataset
uspto-grants-1978_02
Patent number
US04074049

Reaction notes

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