Sodium Iodide → HCID 18936688, compound

HRID 357119Notes

Reaction equation

HRID 357119 reaction equation
[H-].[Na+].[SH:3][C:4]1[N:9]2[CH:10]=[CH:11][N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1.[CH2:13]([C:20]1[C:21](=[O:38])[N:22]([CH2:33][CH2:34][CH2:35][CH2:36]Cl)[C:23](=[O:32])[N:24]2[CH2:29][CH2:28][CH2:27][S:26](=[O:31])(=[O:30])[C:25]=12)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[I-].[Na+]>CN(C)C=O.O>[N:12]1[CH:11]=[CH:10][N:9]2[C:4]([S:3][CH2:36][CH2:35][CH2:34][CH2:33][N:22]3[C:21](=[O:38])[C:20]([CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[C:25]4[S:26](=[O:31])(=[O:30])[CH2:27][CH2:28][CH2:29][N:24]4[C:23]3=[O:32])=[CH:5][CH:6]=[CH:7][C:8]=12

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 18936864HCID 18936864, compoundHCID 178418687HCID 178418687, compound

Product 1

HCID 18936688HCID 18936688, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 0.22 g (5.5 mmol) of 60% oily sodium hydride in 30 ml of N,N-dimethylformamide, 0.83 g (5.5 mmol) of 5-mercaptoimidazo[1,2-a]pyridine was added at room temperature, followed by stirring for 30 minutes. To this mixture, 1.98 g (5 mmol) of 9-benzyl-7-(4-chlorobutyl)-1,1-dioxo-3,4-dihydro-2H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione and 0.82 g (5.5 mmol) of sodium iodide were added, followed by stirring at 100° C. for 2 hours. After cooling, the reaction mixture was poured into water and extracted with ethyl acetate 3 times. The organic layer was washed with water and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, ethyl acetate→ethyl acetate/ethanol=10/1) to yield 1.95 g (78.2%, white powder) of the desired product.

Workup

  1. additionwas added at room temperature
  2. stirringby stirring at 100° C. for 2 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate 3 times
  5. washThe organic layer was washed with water
  6. customdried
  7. distillationafter which the solvent was distilled off
  8. customThe residue was purified by column chromatography (eluent, ethyl acetate→ethyl acetate/ethanol=10/1)

Sources & evidence

ORD record
ord-9643c6b162bb47b9918d25503af21107
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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