1,3-Propanedithiol → 5-(1,3-Dithian-2-yl)-1-methylimidazole

HRID 1646687Notes

Reaction equation

HRID 1646687 reaction equation
[CH:1]([C:3]1[N:7]([CH3:8])[CH:6]=[N:5][CH:4]=1)=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:21]([SH:25])[CH2:22][CH2:23][SH:24]>C1(C)C=CC=CC=1>[S:24]1[CH2:23][CH2:22][CH2:21][S:25][CH:1]1[C:3]1[N:7]([CH3:8])[CH:6]=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 80131,3-PropanedithiolHCID 521998p-Toluenesulfonic acid monohydrateHCID 5735921-methyl-1H-imidazole-5-carbaldehyde

Product 1

HCID 198013405-(1,3-Dithian-2-yl)-1-methylimidazoleYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8.3 g (75.4 mmol) of 5-formyl-1-methylimidazole are dissolved in 120 ml of toluene, and 17.1 g (89.9 mmol) of 4-toluenesulfonic acid monohydrate are added. After addition of 8.12 g (75.0 mmol) of 1,3-propanedithiol, the suspension obtained in this way is boiled under reflux with a water trap. It is subsequently washed with 4N sodium hydroxide solution, and the organic phase is dried over sodium sulfate and concentrated in vacuo until crystallization starts. After storage in a refrigerator overnight, 9.6 g (47.9 mmol, 64%) of 5-(1,3-dithian-2-yl)-1-methylimidazole are obtained as a white solid of melting point 111.5°-112.5° C.

Workup

  1. customthe suspension obtained in this way
  2. temperatureunder reflux with a water trap
  3. washIt is subsequently washed with 4N sodium hydroxide solution
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. concentrationconcentrated in vacuo until crystallization

Sources & evidence

ORD record
ord-e6e671e837e54dbb89a37fde0fd9f684
Source dataset
uspto-grants-1993_01
Patent number
US05180837

Reaction notes

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