Sodium periodate → HCID 178485019, compound

HRID 1438801Notes

Reaction equation

HRID 1438801 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[C:7]([NH:9][C:10]([NH:21][CH3:22])=[N:11][CH2:12][CH2:13][S:14][CH2:15][C:16]1[S:17][CH:18]=[CH:19][N:20]=1)#[N:8]>O>[C:7]([NH:9][C:10]([NH:21][CH3:22])=[N:11][CH2:12][CH2:13][S:14]([CH2:15][C:16]1[S:17][CH:18]=[CH:19][N:20]=1)=[O:2])#[N:8]

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 178484996HCID 178484996, compound

Product 1

HCID 178485019HCID 178485019, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium metaperiodate (220 mg, 1.03 m.mol) was added to a stirred solution of N-cyano-N'-methyl-N"-[2-((2-thiazolyl) methylthio)ethyl]guanidine (255 mg, 1.0 m.mol) in water (90 ml). After 1 hour at 25° then 17 hours at 5° t.l.c. indicated the reaction was essentially complete. The solution was evaporated under reduced pressure at 60° to dryness, with azeotroping with n-propanol (2x). The residue was boiled with isopropanol (20 ml) for 3 minutes, filtered hot from 205 mg of inorganic salts, (100%), and evaporated under reduced pressure to a clear glass which was stirred continuously for 4 days under ether to give crude product (273 mg, 100%) m.p. 110° (softens only). Purification was effected by dissolution in acetonitrite (15 ml) and dilution of the filtered warm solution with ether to 220 ml. After 17 hours standing the precipitate had crystallised yielding, after filtration and washing with ether, N-cyano-N'-methyl-N" -[2-((2-thiazolyl)methylsulphinyl)ethyl]guanidine, (335 mg), m.p. 112°-113° C. Found: C, 39.62; H, 5.03; N, 25.64%. C9H13N5OS2 requires: C, 39.83; H, 4.83; N, 25.81%.

Workup

  1. custom17 hours
  2. customat 5°
  3. customThe solution was evaporated under reduced pressure at 60° to dryness
  4. customwith azeotroping with n-propanol (2x)
  5. waitThe residue was boiled with isopropanol (20 ml) for 3 minutes
  6. filtrationfiltered hot from 205 mg of inorganic salts, (100%)
  7. customevaporated under reduced pressure to a clear glass which

Sources & evidence

ORD record
ord-3c095f22d0604e63be529e99ec5c79cc
Source dataset
uspto-grants-1977_11
Patent number
US04056620

Reaction notes

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