Morpholine → 1,4-Bis(morpholinothio)benzene

HRID 1287206Notes

Reaction equation

HRID 1287206 reaction equation
[C:1]1([SH:8])[CH:6]=[CH:5][C:4]([SH:7])=[CH:3][CH:2]=1.Cl[N:10]1[C:14](=O)[CH2:13][CH2:12][C:11]1=O.S(Cl)Cl.C1(=O)NC(=[O:25])CC1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C1C=CC=CC=1>[O:25]1[CH2:13][CH2:14][N:10]([S:7][C:4]2[CH:5]=[CH:6][C:1]([S:8][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:2][CH:3]=2)[CH2:11][CH2:12]1

Participants

7

Reactant 5

HCID 8083MorpholineHCID 11439SuccinimideHCID 25353Sulfur dichlorideHCID 31398ChlorosuccinimideHCID 46917291,4-Benzenedithiol

Product 1

HCID 215073811,4-Bis(morpholinothio)benzeneYield 70%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

47 g (0.334 mol) of 1,4-benzene dithiol was made into a 30% benzene solution, and then the resulting solution was added dropwise to a solution of 91 g (0.674 mol) of N-chlorosuccinimide in 300 cc of anhydrous benzene at a temperature below 10°C. The resulting sulfenylchloride solution was separated from the by-produced succinimide and 118 g (0.674 mol) of morpholine was added dropwise thereto at a temperature below 10°C. The by-produced morpholine hydrochloride was filtered off and the filtrate was distilled to remove benzene, by which a crude crystal of 1,4-bis(morpholinothio)benzene was obtained. This crude crystal was recrystallized and purified from ethanol. The purified crystal had a melting point of 95°C, and the yield was 70%. It was identified from NMR, IR and elementary analysis that the crystal is 1,4-bis(morpholinothio)benzene.

Workup

  1. additionwas added dropwise
  2. customat a temperature below 10°C
  3. filtrationThe by-produced morpholine hydrochloride was filtered off
  4. distillationthe filtrate was distilled
  5. customto remove benzene

Sources & evidence

ORD record
ord-c3af0e5c2f034cf5a77c5f9d0158d69a
Source dataset
uspto-grants-1976_10
Patent number
US03984383

Reaction notes

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