Water → HCID 86734204, compound

HRID 1730576Notes

Reaction equation

HRID 1730576 reaction equation
[CH2:1](I)[CH3:2].[CH2:4]1[O:23][C:7]2([C:12]3[CH:13]=[CH:14][C:15]4[C:20]([C:11]=3[S:10](=[O:22])(=[O:21])[NH:9][CH2:8]2)=[CH:19][CH:18]=[CH:17][CH:16]=4)[O:6][CH2:5]1.[OH-].[Na+].O>C(O)(C)C>[CH2:4]1[O:23][C:7]2([C:12]3[CH:13]=[CH:14][C:15]4[C:20]([C:11]=3[S:10](=[O:22])(=[O:21])[N:9]([CH2:1][CH3:2])[CH2:8]2)=[CH:19][CH:18]=[CH:17][CH:16]=4)[O:6][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 14798Sodium HydroxideHCID 86734203HCID 86734203, compound

Product 1

HCID 86734204HCID 86734204, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

15.6 gm (0.1 mol) of ethyl iodide were added dropwise in several portions to a solution of 10.0 gm (0.034 mol) of 2H-naphtho[2,1-e]-1,2-thiazine-4(3H)-one-1,1-dioxide-ethylene ketal in a mixture of 150 ml of isopropanol, 36 ml of 1 N sodium hydroxide and 36 ml of water, while stirring. Stirring was continued for 84 hours, whereupon the mixture was evaporated in vacuo, the residue was taken up in methylenechloride, and the solution was washed with water, dried and evaporated. 10.9 gm (99% of theory) of 2-ethyl-2H-naphtho[2,1-e]-1,2-thiazine-4(3H)-one-1,1-dioxide-ethylene ketal were obtained, which were used as such in the next reaction step.

Workup

  1. stirringStirring
  2. customwas evaporated in vacuo
  3. washthe solution was washed with water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-7cdf4e3f987c4d0ca18f3ca357cff0df
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

Loading…