Iodoethane → 2-Ethyl-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide

HRID 1730564Notes

Reaction equation

HRID 1730564 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]([C:7]1[NH:8][S:9](=[O:23])(=[O:22])[C:10]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][C:11]=2[C:12]=1[OH:13])=[O:6].[CH2:24](I)[CH3:25]>C(O)C>[CH3:3][O:4][C:5]([C:7]1[N:8]([CH2:24][CH3:25])[S:9](=[O:23])(=[O:22])[C:10]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][C:11]=2[C:12]=1[OH:13])=[O:6]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 547193904-hydroxy-2H-naphtho[2,1-e]-1,2thiazine-3-carboxylic acid methyl ester-1,1-dioxide

Product 1

HCID 681427532-Ethyl-4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

33 ml of 1 N sodium hydroxide were added dropwise over a period of 25 minutes to a suspension of 10.1 gm (0.033 mol) of 4-hydroxy-2H-naphtho[2,1-e]-1,2-thiazine-3-carboxylic acid methyl ester-1,1-dioxide and 20 gm (0.12 mol) of ethyl iodide in 400 ml of aqueous 75% ethanol, whereby the starting material went completely into solution. The reaction mixture was then stirred at room temperature for 30hours. Thereafter, the crystals which had formed were collected by filtration and washed with a small quantity of ethanol, yielding 8.7 gm (79% of theory) of the desired compound, m.p. 179° C (from ethanol).

Workup

  1. customThereafter, the crystals which had formed
  2. filtrationwere collected by filtration
  3. washwashed with a small quantity of ethanol

Sources & evidence

ORD record
ord-63a939e89a84494093d178135c979816
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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