Diisopropylethylamine → 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide

HRID 1289831Notes

Reaction equation

HRID 1289831 reaction equation
[CH:1]([C:4]1[C:9]2[C:10](=[O:15])[NH:11][S:12](=[O:14])(=[O:13])[C:8]=2[CH:7]=[C:6]([O:16][CH3:17])[CH:5]=1)([CH3:3])[CH3:2].[C:18](OCCl)(=O)C(C)(C)C.C(N(C(C)C)CC)(C)C.[BrH:36].C(O)(=O)C>C(#N)C>[Br:36][CH2:18][N:11]1[C:10](=[O:15])[C:9]2[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][C:6]([O:16][CH3:17])=[CH:7][C:8]=2[S:12]1(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 87885Chloromethyl pivalateHCID 101473624-Isopropyl-6-methoxysaccharinHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 108825772-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxideYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture 4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (0.51 g, 2 mmol), acetonitrile (5.0 ml), chloromethyl pivalate (0.32 ml, 2.2 mmol) and diisopropylethylamine (0.42 ml, 2.4 mmol) was heated to reflux until the starting material was consumed and then 33% HBr/acetic acid (2.4 g, 10 mmol) was added and the mixture was refluxed for 15 minutes. The reaction mixture was coooled, quenched with ice-water and filtered to afford 0.42 g (65%) of 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide, m.p. 158°-160.5° C., after recrystallization from ethyl acetate/hexane (3/2).

Workup

  1. temperatureto reflux until the starting material
  2. customwas consumed
  3. temperaturethe mixture was refluxed for 15 minutes
  4. customquenched with ice-water
  5. filtrationfiltered

Sources & evidence

ORD record
ord-60952cffffd8454fa21f2c10410abc04
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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