Methyl iodide → 4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-naphtho [2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

HRID 1730571Notes

Reaction equation

HRID 1730571 reaction equation
[OH-].[Na+].[OH:3][C:4]1[C:9]2[CH:10]=[CH:11][C:12]3[C:17]([C:8]=2[S:7](=[O:19])(=[O:18])[NH:6][C:5]=1[C:20]([NH:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1)=[O:21])=[CH:16][CH:15]=[CH:14][CH:13]=3.[CH3:28]I>CO>[OH:3][C:4]1[C:9]2[CH:10]=[CH:11][C:12]3[C:17]([C:8]=2[S:7](=[O:19])(=[O:18])[N:6]([CH3:28])[C:5]=1[C:20]([NH:22][C:23]1[S:24][CH:25]=[CH:26][N:27]=1)=[O:21])=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 546959454-Hydroxy-N-(2-thiazolyl)-2H-naphtho-[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide

Product 1

HCID 547184104-hydroxy-2-methyl-N-(2-thiazolyl)-2H-naphtho [2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxideYield 40.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.15 ml of 1 N sodium hydroxide (3.15 millimols) were added dropwise to a suspension of 1.12 gm (3 millimols) of 4-hydroxy-N-(2-thiazolyl) 2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide in 50 ml of methanol and 1.7 gm (12 millimols) of methyl iodide, whereby a reddish solution was formed. The solution was stirred at room temperature for 72 hours and was then evaporated to dryness in vacuo. The residue was triturated with water, filterd off and recrystallized from ethylene chloride, yielding 0.47 gm (40.5% of theory) of 4-hydroxy-2-methyl-N-(2-thiazolyl)-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide, m.p. 249°-250° C (decomp).

Workup

  1. customwas formed
  2. customwas then evaporated to dryness in vacuo
  3. customThe residue was triturated with water, filterd off and
  4. customrecrystallized from ethylene chloride

Sources & evidence

ORD record
ord-1909ea5b44df4dc9b74c1a31c41b4cc1
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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