Potassium Iodide → HCID 23287681, compound

HRID 367221Notes

Reaction equation

HRID 367221 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([NH:6][C:7]2[S:8][C:9]3[N:17]=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[N:12]=2)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[I-].[K+].Br[CH2:29][CH:30]1[O:34][CH2:33][CH2:32][O:31]1>CS(C)=O>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]=[C:7]2[N:12]([CH2:29][CH:30]3[O:34][CH2:33][CH2:32][O:31]3)[C:11](=[O:13])[C:10]3[CH:14]=[CH:15][CH:16]=[N:17][C:9]=3[S:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 780681,3-Dioxolane, 2-(bromomethyl)-HCID 42920704H-Pyrido[3,2-e]-1,3-thiazin-4-one, 2-[(4-chlorophenyl)amino]-HCID 23665647Potassium tert-butoxide

Product 1

HCID 23287681HCID 23287681, compoundYield 9.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In an atmosphere of argon, a mixture of 290 mg (1.0 mmol) of 2-(4-chloroanilino)-4H-pyrido[3,2-e]-1,3-thiazin-4-one and 1.4 ml of DMSO was put in a 30 ml flask. To the mixture was then added 113 mg (1.0 mmol) of potassium t-butoxide with stirring. The mixture was then stirred for 1 hour. To the mixture was then added 10 mg (0.06 eq) of potassium iodide. To the mixture was then added 484 mg of 2-bromomethyl-1,3-dioxolane. The mixture was then stirred for 15 hours. After the termination of reaction, the reaction mixture was extracted with water and ethyl acetate. The resulting organic phase was separated, washed with water and saturated brine, and then dried over sodium sulfate. The drying agent was then removed by filtration. The filtrate was then concentrated under reduced pressure. The resulting residue was then purified through silica gel column chromatography (eluant: 1/2 mixture of ethyl acetate and normal hexane). As a result, 36 mg of 2-[(4-chlorophenyl)imino]-3-([1,3]dioxolan-2-ylmethyl)-2,3-dihydro-4H-pyrido[3,2-e]-1,3-thiazin-4-one was obtained as a low polarity substance, and 20 mg of 2-[N-(4-chlorophenyl)-N-([1,3]dioxolan-2-ylmethyl)amino]-4H-pyrido[3,2-e]-1,3-thiazin-4-one was obtained as a high polarity substance.

Workup

  1. customwas put in a 30 ml flask
  2. stirringThe mixture was then stirred for 1 hour
  3. stirringThe mixture was then stirred for 15 hours
  4. customAfter the termination of reaction
  5. extractionthe reaction mixture was extracted with water and ethyl acetate
  6. customThe resulting organic phase was separated
  7. washwashed with water and saturated brine
  8. dry with materialdried over sodium sulfate
  9. customThe drying agent was then removed by filtration
  10. concentrationThe filtrate was then concentrated under reduced pressure
  11. customThe resulting residue was then purified through silica gel column chromatography (eluant: 1/2 mixture of ethyl acetate and normal hexane)

Sources & evidence

ORD record
ord-3c0d24e2fc4d4946bcc6505ab60a0dcf
Source dataset
uspto-grants-2000_10
Patent number
US06133258

Reaction notes

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