Iodoethane → 2-Ethyl-4-hydroxy-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide

HRID 224608Notes

Reaction equation

HRID 224608 reaction equation
[CH2:1](I)[CH3:2].[OH:4][C:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8](=[O:16])(=[O:15])[NH:7][C:6]=1[C:17]([NH:19][C:20]1[S:21][C:22]([CH3:25])=[CH:23][N:24]=1)=[O:18]>CO.[OH-].[Na+]>[CH2:1]([N:7]1[C:6]([C:17]([NH:19][C:20]2[S:21][C:22]([CH3:25])=[CH:23][N:24]=2)=[O:18])=[C:5]([OH:4])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8]1(=[O:16])=[O:15])[CH3:2]

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 546906574-Hydroxy-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide

Product 1

HCID 546901382-Ethyl-4-hydroxy-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxideYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

0.94 gm (6 millimols) of ethyl iodide were added to a solution of 0.7 gm (2 millimols) of 4-hydroxy-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide in 30 ml of methanol and 2.0 ml of 1N sodium hydroxide. The reaction mixture was stirred for 24 hours at room temperature, then neutralized and evaporated in vacuo. The residue was purified by column chromatography (Merck-silica gel 60, particle size: 0.2-0.5 mm; eluant: chloroform/ethanol 95:5), yielding 0.35 mgm (48% of theory) of 2-ethyl-4-hydroxy-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide after recrystallization from xylene.

Workup

  1. customevaporated in vacuo
  2. customThe residue was purified by column chromatography (Merck-silica gel 60, particle size: 0.2-0.5 mm; eluant: chloroform/ethanol 95:5)

Sources & evidence

ORD record
ord-7e8dbc42e9ab41089cf19bcbf3bdcc76
Source dataset
uspto-grants-1980_11
Patent number
US04233299

Reaction notes

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