3,4-Toluenedithiol → HCID 21163763, compound

HRID 1278336Notes

Reaction equation

HRID 1278336 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([SH:9])[C:5]([SH:8])=[CH:6][CH:7]=1.[OH-:10].[Na+].[Cl:12][CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>O>[ClH:12].[ClH:12].[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[C:4]([S:9][CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:10][CH2:18][CH2:17]2)[CH:3]=1

Participants

5

Reactant 3

HCID 103343,4-ToluenedithiolHCID 14798Sodium HydroxideHCID 958344-(3-Chloropropyl)morpholine

Product 1

HCID 21163763HCID 21163763, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a warm (60° C.) solution of 10.0 g (0.0640 mole) of 4-methyl-o-benzenedithiol, 5.12 g (0.128 mole) of sodium hydroxide in 70 ml of water was added 21.0 g (0.128 mole) of 4-(3-chloropropyl)morpholine. The reaction mixture was stirred at 60° to 65° C. for 30 minutes, cooled and extracted with methylene chloride. After the extract was dried over anhydrous magnesium sulfate and filtered, ethanolic hydrogen chloride was added, and the solvent and excess hydrogen chloride were removed by evaporation in vacuo. The oily residue was crystallized from propanol-2. Recrystallization from methanol-propanol-2 (1.4:1) gave the product, 4,4'-((4-methyl-1,2-phenylene)bis(thio-3,1-propanediyl))bismorpholine dihydrochloride as white crystals, m.p. 233-234° C.

Workup

  1. temperaturecooled
  2. extractionextracted with methylene chloride
  3. dry with materialAfter the extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. additionethanolic hydrogen chloride was added
  6. customthe solvent and excess hydrogen chloride were removed by evaporation in vacuo
  7. customThe oily residue was crystallized from propanol-2
  8. customRecrystallization from methanol-propanol-2 (1.4:1)

Sources & evidence

ORD record
ord-006ac67a4d3d466db8e2c8f6bb6ff627
Source dataset
uspto-grants-1981_07
Patent number
US04281118

Reaction notes

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