Sodium periodate → HCID 178485020, compound

HRID 127180Notes

Reaction equation

HRID 127180 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[C:7]([NH:9][C:10]([NH:22][CH3:23])=[N:11][CH2:12][CH2:13][S:14][CH2:15][C:16]1[NH:20][CH:19]=[N:18][C:17]=1[CH3:21])#[N:8]>O>[C:7]([NH:9][C:10]([NH:22][CH3:23])=[N:11][CH2:12][CH2:13][S:14]([CH2:15][C:16]1[NH:20][CH:19]=[N:18][C:17]=1[CH3:21])=[O:2])#[N:8]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 178485005Cimetidine

Product 1

HCID 178485020HCID 178485020, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium metaperiodate (1.85 g, 8.68 m.mol.) was added to a stirred, cooled (5°) solution of N-cyano-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine (2.085 g, 8.27 m.mol.) in water (83 ml). After 90 minutes stirring at 5° thin layer chromatography indicated almost complete disappearance of starting material. The solution was allowed to stand overnight at room temperature to complete the reaction, then evaporated under reduced pressure to dryness, with azeotroping with n-propanol. The residue was boiled with isopropanol (60 ml), filtered hot, and the filtrate was evaporated to dryness to give the crude product as a glass. This was purified by charcoaling in methanol (40 ml), filtration and dilution with ether to 1500 ml. The liquid was decanted from the flocculent precipitated glass which was kept under a further 1500 ml ether to become semicrystalline, then filtered and allowed to stand overnight in air. The hardened glass was stirred with cold methanol (25 ml) filtered from insoluble crude product and and inorganics (0.28 g. m.p. 190°) and to the filtrate was carefully added ether (to 500 ml) so that two layers formed. On standing undisturbed for three days there separated off white crystals of N-cyano-N'-methyl-N"-[2-((4-methyl-5-imidazolyl)methylsulphinyl)ethyl]guanidine (1.55 g), m.p. 185°-186.5° C. Found: C, 44.57; N, 6.08; N, 31.18; S, 11.91% C10H16N6OS requires C, 44.76; H, 6.01; N, 31.32; S, 11.95%.

Workup

  1. waitto stand overnight at room temperature
  2. customthe reaction
  3. customevaporated under reduced pressure to dryness
  4. customwith azeotroping with n-propanol
  5. filtrationfiltered hot
  6. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-290c030bd49842228cb2ca1231758b84
Source dataset
uspto-grants-1981_03
Patent number
US04255425

Reaction notes

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