Methyl iodide → HCID 13686311, compound

HRID 1731250Notes

Reaction equation

HRID 1731250 reaction equation
[Cl:1][C:2]1[C:10]2[S:9](=[O:12])(=[O:11])[NH:8][CH2:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH3:13]C(C)([O-])C.[K+].CI>CN(C)C=O>[CH3:13][N:8]1[CH2:7][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:10]=2[S:9]1(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 136863107-Chloro-2,3-dihydrobenzo[d]isothiazole 1,1-DioxideHCID 23665647Potassium tert-butoxide

Product 1

HCID 13686311HCID 13686311, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 16.6 g of 7-chloro-2,3-dihydro-1,2-benzisothiazole-1,1-dioxide in 85 mls of dry dimethylformamide was cooled and treated with 10 g of potassium t-butoxide at such a rate that the temperature remained below 6° C. The resulting suspension was stirred at 5° to 10° C. for 30 minutes, treated with 6.1 mls of methyl iodide at 10° to 15° C. and stirred at room temperature for 16 hours. The mixture was poured into ice water and the resulting solid was filtered, washed with water and dried in vacuo at 50° C. for 1.5 hours to give 15.4 g of the title compound as a pinkish solid, m.p. 95°-97° C.

Workup

  1. customremained below 6° C
  2. stirringstirred at room temperature for 16 hours
  3. filtrationthe resulting solid was filtered
  4. washwashed with water
  5. customdried in vacuo at 50° C. for 1.5 hours

Sources & evidence

ORD record
ord-c6450c1be7d943668e8e3ebdad0d82d5
Source dataset
uspto-grants-1986_11
Patent number
US04620870

Reaction notes

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