Sodium Iodide → 2-Benzyl-5-(N,N-dimethylthiocarbamoyl)thio-4-isothiazolin-3-one

HRID 1105879

Reaction equation

HRID 1105879 reaction equation
[CH2:1]([N:8]1[C:12](=[O:13])[CH:11]=[C:10](Cl)[S:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Na+].[CH3:18][N:19]([CH3:23])[C:20](=[S:22])[S-:21].[I-].[Na+]>C(O)C>[CH2:1]([N:8]1[C:12](=[O:13])[CH:11]=[C:10]([S:22][C:20](=[S:21])[N:19]([CH3:23])[CH3:18])[S:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 43451522-benzyl-5-chloroisothiazol-3(2H)-oneHCID 23693613Sodium dimethyldithiocarbamate dihydrate

Product 1

HCID 128527272-Benzyl-5-(N,N-dimethylthiocarbamoyl)thio-4-isothiazolin-3-oneYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 6.76 g. (0.03 mole) of 2-benzyl-5-chloro-4-isothiazolin-3-one in 25 ml of ethanol was added a solution of 5.37 g. (0.03 mole) of N,N-dimethyldithiocarbamic acid sodium salt dihydrate in 30 ml of ethanol followed by 0.1 g. of sodium iodide. A yellow solid separated spontaneously. The mixture was stirred at room temperature for 3 hours, then cooled and filtered. The solid was triturated with 50 ml of water and recrystallized from 250 ml of boiling EtOH to give 5.6 g. (60% yield) of the named product, mp 184°-186°.

Workup

  1. customA yellow solid separated spontaneously
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe solid was triturated with 50 ml of water
  5. customrecrystallized from 250 ml of boiling EtOH
  6. customto give 5.6 g

Sources & evidence

ORD record
ord-7418178551d446d4aeac9a32f44bb6f8
Source dataset
uspto-grants-1982_01
Patent number
US04310590

Linked notes

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