Carbon Disulfide → 4-((Morpholinothio)thioxomethyl)morpholine

HRID 435835Notes

Reaction equation

HRID 435835 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl-].Cl[N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.[C:15](=[S:17])=[S:16].[OH-].[Na+].[O-]Cl.[Na+]>CO.C(Cl)(Cl)Cl.O>[CH2:6]1[N:1]([C:15]([S:17][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[S:16])[CH2:2][CH2:3][O:4][CH2:5]1

Participants

9

Reactant 5

HCID 6348Carbon Disulfide2×HCID 8083Morpholine2×HCID 14798Sodium HydroxideHCID 21481729HCID 21481729, compoundHCID 23665760Sodium Hypochlorite

Product 1

HCID 837004-((Morpholinothio)thioxomethyl)morpholine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6212ChloroformSolvent3×

Conditions

Temperature
0 °C

Procedure

N-oxydiethylenethiocarbamyl-N'-oxydiethylenesulfenamide was prepared by reacting about 0.2 mole of morpholine and about 0.2 mole of N-chloromorpholine chloride with 0.2 mole of carbon disulfide in the presence of about 0.2 mole of NaOH and in a medium of water and chloroform. 34.8 grams (0.4 mole) of morpholine was added to 50 milliliters of chloroform and the solution cooled to 0° C. 110 grams of a solution of NaOCl at 13% by weight in water (0.2 mole) was added and the mixture stirred for 10 minutes at a temperature of about 10° C. 15.2 grams (0.2 mole) of carbon disulfide was then added and the mix stirred for 10 minutes at 10°±5° C. The mixture became thick and an additional 50 milliliters of chloroform was added. After 15 minutes of stirring, the mixture was allowed to settle and the non-aqueous phase was separated out. The chloroform was evaporated off under reduced pressure. The pale yellow crystals obtained were slurried in methanol, filtered out and dried. The yield of compound was 45.2 grams, 92% by weight of theoretical. The compound was identified by its IR spectrum, and it had a melting point of 128°-134° C.

Workup

  1. stirringthe mix stirred for 10 minutes at 10°±5° C
  2. stirringAfter 15 minutes of stirring
  3. customthe non-aqueous phase was separated out
  4. customThe chloroform was evaporated off under reduced pressure
  5. customThe pale yellow crystals obtained
  6. filtrationfiltered out
  7. customdried

Sources & evidence

ORD record
ord-31cafa9e8abb43619d701fd80725320e
Source dataset
uspto-grants-1977_02
Patent number
US04006251

Reaction notes

Loading…