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

HRID 1730569Notes

Reaction equation

HRID 1730569 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[NH:14][S:15](=[O:29])(=[O:28])[C:16]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][C:17]=3[C:18]=2[OH:19])=[O:12])[CH:7]=[CH:8][CH:9]=1.[CH3:30]I>CO>[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[N:14]([CH3:30])[S:15](=[O:28])(=[O:29])[C:16]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][C:17]=3[C:18]=2[OH:19])=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 54695941N-(3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]1,2-thiazine-3-carboxamide-1,1-dioxide

Product 1

HCID 54695958N-(3-Chloro-phenyl)-4-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxideYield 64.3%

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 1.2 gm (3 millimols) of N-(3-chloro-phenyl)-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide in 100 ml of methanol and 1.7 gm (12 millimols) of methyl iodide. The resulting mixture was stirred at room temperature for 72 hours, and was then evaporated to dryness in vacuo. The residue was washedwith a small quantity of water, and the remaining solid matter was recrystallized from ethylene chloride, yielding 0.8 gm (64% of theory) of N-(3-chloro-phenyl)-4-hydroxy-2-methyl-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxamide-1,1-dioxide, m.p. 248°-249° C (decomp.).

Workup

  1. customwas then evaporated to dryness in vacuo
  2. customthe remaining solid matter was recrystallized from ethylene chloride

Sources & evidence

ORD record
ord-b43cd8d106054a39b300429aa6b11627
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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