2-Methyl-3,4,5-trichloroisothiazolium methylsulfate → 4,5-Dichloro-2-methyl-4-isothiazolin-3-thione

HRID 1905046Notes

Reaction equation

HRID 1905046 reaction equation
CO[S:3]([O-])(=O)=O.[CH3:7][N+:8]1[S:9][C:10]([Cl:15])=[C:11]([Cl:14])[C:12]=1Cl>C(O)C>[Cl:14][C:11]1[C:12](=[S:3])[N:8]([CH3:7])[S:9][C:10]=1[Cl:15]

Participants

3

Reactant 1

HCID 128890232-Methyl-3,4,5-trichloroisothiazolium methylsulfate

Product 1

HCID 128890534,5-Dichloro-2-methyl-4-isothiazolin-3-thioneYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methyl-3,4,5-trichloroisothiazolium methylsulfate (10.7 g) thiourea (2.6 g) were added to 100 ml of ethanol at room temperature. After stirring overnight the product which had precipitated from solution was collected by filtration and recrystallized from ethanol to yield 5.3 g (78%) of 4,5-dichloro-2-methyl-4-isothiazolin-3-thione, mp 143-144. Analysis: Calculated for C4H3ClNS2 : C, 24.00; H, 1.50; N, 7.00; Cl, 35.45; S, 32.05. Found: C, 24.07; H, 1.45; N, 7.00; Cl, 35.67; S, 31.78.

Workup

  1. customhad precipitated from solution
  2. filtrationwas collected by filtration
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-fb10ae65dd6348a6bb4a5a66330c7090
Source dataset
uspto-grants-1989_06
Patent number
US04841063

Reaction notes

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