1,3-Benzodioxole → 3,4-Methylenedioxyphenyl thiocyanate

HRID 465504Notes

Reaction equation

HRID 465504 reaction equation
[Pb](SC#N)[S:2][C:3]#[N:4].ClCl.[CH2:10]1[O:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11]1>C(O)(=O)C>[CH2:10]1[O:18][C:13]2[CH:14]=[CH:15][C:16]([S:2][C:3]#[N:4])=[CH:17][C:12]=2[O:11]1

Participants

5

Reactant 3

HCID 92291,3-BenzodioxoleHCID 24526ChlorineHCID 516874Bleirhodanid

Product 1

HCID 130901463,4-Methylenedioxyphenyl thiocyanateYield 161.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Lead thiocyanate (45 g, 139 mmol) was added in portions to a stirred solution of chlorine (20.3 g, 290 mmol) in anhydrous acetic acid (600 ml) under an atmosphere of argon. The mixture was stirred for 15 minutes. 1,2-Methylenedioxybenzene (35 g, 286 mmol) was added in one portion. The mixture was stirred for 1 hour and then filtered. The filtrate was added to ice-water (3.5 liters). The precipitated solid was collected by filtration, dissolved in ethyl acetate and dried (MgSO4). The solvent was removed by evaporation to give 3,4-methylenedioxyphenyl thiocyanate as a pale green oil (40.3 g, 79% yield). The oil solidified and was used without further purification or characterisation.

Workup

  1. stirringThe mixture was stirred for 1 hour
  2. filtrationfiltered
  3. additionThe filtrate was added to ice-water (3.5 liters)
  4. filtrationThe precipitated solid was collected by filtration
  5. dissolutiondissolved in ethyl acetate
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-2b29afe25d874014b8519af5d51dde89
Source dataset
uspto-grants-1992_10
Patent number
US05153227

Reaction notes

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