Methyl iodide → 2-Methyl-1,2-benzoisothiazolin-3-one

HRID 335504Notes

Reaction equation

HRID 335504 reaction equation
[Li].[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])[NH:3]1.[CH3:12]I>C1COCC1>[CH3:12][N:3]1[C:4](=[O:11])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[S:2]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 70348857111337-53-22×

Product 1

HCID 3512362-Methyl-1,2-benzoisothiazolin-3-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 1,2-benzisothiazolin-3-one lithium salt in THF (3 ml per gram of BIT salt) was added methyl iodide (1.1 molar equivalents). The resulting slurry was stirred at ambient temperature for 72 hours. HPLC analysis showed greater than 97% alkylation of 1,2-benzisothiazolin-3-one lithium salt. The mixture was allowed to cool and the crude product isolated as a mixture of N-methyl-1,2-benzisothiazolin-3-one and 3-methoxy-1,2-benzisothiazolin-3-one in 98.8:1.2 ratio.

Workup

  1. temperatureto cool

Sources & evidence

ORD record
ord-bad24296debe4b55aa17dc499c20025f
Source dataset
uspto-grants-2014_11
Patent number
US08884024B1

Reaction notes

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