Sodium periodate → HCID 86738860, compound

HRID 851147Notes

Reaction equation

HRID 851147 reaction equation
[C:1]1([C:7]2[NH:11][C:10]3[C:12]([CH3:20])([CH3:19])[CH2:13][S:14][CH2:15][C:16]([CH3:18])([CH3:17])[C:9]=3[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I([O-])(=O)(=O)=[O:22].[Na+]>CO.O>[C:1]1([C:7]2[NH:11][C:10]3[C:12]([CH3:20])([CH3:19])[CH2:13][S:14](=[O:22])[CH2:15][C:16]([CH3:18])([CH3:17])[C:9]=3[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 86738861HCID 86738861, compound

Product 1

HCID 86738860HCID 86738860, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
2 °C

Procedure

1.43 g of 2-phenyl-4,5,7,8-tetrahydro-4,4,8,8-tetramethyl-1-H-thiepino[4,5-d]imidazole are dissolved in 75 ml of methanol and cooled to 2° C. with stirring. The solution is treated dropwise at this temperature with a solution of 1.3 g of sodium periodate in 28 ml of water. The mixture is left to react-out at the same temperature for 3 hours. Thereupon, 25 ml of methanol are added. After stirring for 5 hours at room temperature, the solution is concentrated. The product is left to crystallize-out while cooling with ice. The precipitate is removed by filtration and the crystals are covered with acetone and ether. After filtration, the 2-phenyl-4,5,7,8-tetrahydro-4,4,8,8-tetramethyl-1-H-thiepino-[4,5-d]-imidazole 6-oxide is recrystallized from ethanol/n-hexane, m.p. 273°-275° C.; m.p. of the hydrochloride: 300° C.

Workup

  1. waitThe mixture is left
  2. customto react-out at the same temperature for 3 hours
  3. stirringAfter stirring for 5 hours at room temperature
  4. concentrationthe solution is concentrated
  5. waitThe product is left
  6. customto crystallize-out
  7. temperaturewhile cooling with ice
  8. customThe precipitate is removed by filtration
  9. filtrationAfter filtration
  10. customthe 2-phenyl-4,5,7,8-tetrahydro-4,4,8,8-tetramethyl-1-H-thiepino-[4,5-d]-imidazole 6-oxide is recrystallized from ethanol/n-hexane, m.p. 273°-275° C.
  11. custom300° C.

Sources & evidence

ORD record
ord-0f3a43776cfa4413b95ae20697a829d6
Source dataset
uspto-grants-1983_05
Patent number
US04382945

Reaction notes

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