Sodium Iodide → 5-(N,N-Dimethylthiocarbamoyl)thio-4-methyl-2-phenyl-4-isothiazolin-3-one

HRID 1105880

Reaction equation

HRID 1105880 reaction equation
Cl[C:2]1[S:6][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4](=[O:13])[C:3]=1[CH3:14].[CH3:15][N:16]([CH3:20])[C:17](=[S:19])[SH:18].[Na].[I-].[Na+]>C(O)C>[CH3:15][N:16]([CH3:20])[C:17]([S:19][C:2]1[S:6][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4](=[O:13])[C:3]=1[CH3:14])=[S:18]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6599Dimethyldithiocarbamic acidHCID 5360545SodiumHCID 198761675-chloro-4-methyl-2-phenylisothiazol-3(2H)-one

Product 1

HCID 128527285-(N,N-Dimethylthiocarbamoyl)thio-4-methyl-2-phenyl-4-isothiazolin-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 4.51 g. (0.02 mole) of 5-chloro-4-methyl-2-phenyl-4-isothiazolin-3-one in 30 ml of warm ethanol was added a solution of 3.58 g. (0.02 mole) of N,N-dimethyldithiocarbamic acid, sodium salt dihydrate in 20 ml of ethanol followed by 0.1 g. of sodium iodide. The mixture was stirred several hours, cooled and filtered. The solid was triturated with water and dried to give 5.3 g. (88%) of the named product, mp 158°-160°.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customThe solid was triturated with water
  4. customdried
  5. customto give 5.3 g

Sources & evidence

ORD record
ord-14fd87cf8fe5449984c02e859ec68e5d
Source dataset
uspto-grants-1982_01
Patent number
US04310590

Linked notes

Loading…