Hydrogen Sulfide → 2-Imino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine

HRID 5320

Reaction equation

HRID 5320 reaction equation
[C:1]([N:3]([CH2:14][C:15]#[CH:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[CH:5]=1)#[N:2].C(N(CC)CC)C.[SH2:24]>CO>[NH:2]=[C:1]1[N:3]([C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[CH:5]=2)[CH2:14][C:15](=[CH2:16])[S:24]1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 22416968N-cyano-N-propargyl-3-trifluoromethylaniline

Product 1

HCID 152396762-Imino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-cyano-3-trifluoromethylaniline (5.0 g) in acetone (100 ml), potassium carbonate (7.4 g) and propargyl bromide (3.5 g) were added, and the resultant mixture was stirred at room temperature for 10 hours, followed by filtration of the reaction mixture. The solvent was removed from the filtrate by distillation under reduced pressure, and the residue was subjected to column chromatography to give N-cyano-N-propargyl-3-trifluoromethylaniline (3.8 g). The thus obtained N-cyano-N-propargyl-3-trifluoromethylaniline (1 g) and a catalytic amount of triethylamine were dissolved in methanol (30 ml), and the resultant mixture was cooled to 0° C. Hydrogen sulfide was gradually introduced into the mixture for 20 minutes while keeping the temperature at 0° C., followed by introduction of nitrogen gas to remove hydrogen sulfide. The solvent was removed by distillation, and the residue was subjected to column chromatography to give 0.2 g of 2-imino-3-(3-trifluoromethylphenyl)-5-methylenethiazolidine (Compound (ix)).

Workup

  1. customat 0° C.
  2. customto remove hydrogen sulfide
  3. customThe solvent was removed by distillation

Sources & evidence

ORD record
ord-270b39e5107f474fb7cc4aaffd104d14
Source dataset
uspto-grants-1993_09
Patent number
US05244863

Linked notes

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