HCID 86736276, compound → HCID 22750003, compound

HRID 2164114Notes

Reaction equation

HRID 2164114 reaction equation
C1O[C:4]2([C:9]3[N:10]([CH3:17])[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=4[C:8]=3[S:7](=[O:19])(=[O:18])[N:6]([CH3:20])[CH2:5]2)[O:3]C1>Cl.CO>[CH3:20][N:6]1[CH2:5][C:4](=[O:3])[C:9]2[N:10]([CH3:17])[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:8]=2[S:7]1(=[O:19])=[O:18]

Participants

4

Reactant 1

HCID 86736276HCID 86736276, compound

Product 1

HCID 22750003HCID 22750003, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

2.2 gm (7.4 millimols) of 2,5-dihydro-2,5-dimethyl-1,2-thiazino[5,6-b]-indole-4(3H)-one-1,1-dioxide-ethylene ketal were refluxed for one hour in a mixture of 60 ml of 9% hydrochloric acid and 60 ml of methanol. Subsequently, the mixture was evaporated to dryness in vacuo. After taking up the residue in methylene chloride, washing the solution with water, drying and evaporating it, and recrystallizing the raw product from ethanol, 1.6 gm (82% of theory) of 2,5-dihydro-2,5-dimethyl-1,2-thiazino-[5,6-b]indole-4(3H)-one-1,1-dioxide were obtained; M.p.: 180° C.; 1H-NMR (CDCl3): δ = 8.0 (m, 1) and 7.4 (m, 3; arom. H) 4.15 (s, 2, CH2); 4.06 (s, 3, 5-CH3); 3.00 (s, 3, 2-CH3).

Workup

  1. customSubsequently, the mixture was evaporated to dryness in vacuo
  2. washwashing the solution with water
  3. customdrying
  4. customevaporating it
  5. customrecrystallizing the raw product from ethanol

Sources & evidence

ORD record
ord-a7f1a209946d4ff3bc160096aebbf2f0
Source dataset
uspto-grants-1979_01
Patent number
US04137313

Reaction notes

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