Sodium Hydroxide → 5-Guanidino-1,2,4-thiadiazole

HRID 1733490Notes

Reaction equation

HRID 1733490 reaction equation
C(N=C(NC)NCCSC[C:10]1[N:14]=[C:13]([NH:15][C:16]([NH2:18])=[NH:17])[S:12][N:11]=1)#N.[OH-].[Na+]>Cl>[NH:15]([C:13]1[S:12][N:11]=[CH:10][N:14]=1)[C:16]([NH2:18])=[NH:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178485071HCID 178485071, compound

Product 1

HCID 1785127325-Guanidino-1,2,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 3-[-2-(2-cyano-3-methylguanidino)ethylthiomethyl]-5-guanidino-1,2,4-thiadiazole (0.2 g.) and 1 N hydrochloric acid (50 ml.) was heated under reflux for 30 minutes, cooled, neutralised with 1 N sodium hydroxide and extracted with ethyl acetate (6×25 ml.). The combined extracts were dried (MgSO4) and evaporated in vacuo to a white solid which was dissolved in ethanol (3 ml.) and added to a solution of oxalic acid (0.071 g.) in ethanol (2 ml.). The precipitated solid was filtered off, washed with ethanol and dried at 50°/0.1 m.m. to give 3-8 2-(2-carbamoyl-3-methylguanidino)ethylthiomethyl]-5-guanidino-1,2,4-thiadiazole. 1.75 oxalate. Found: C, 31.0; H, 4.3; N, 25.7; S, 13.5; C9H17N9OS2. 1.75C2H2O4 requires C, 30.7; H, 4.2; N, 25.8; S, 13.1%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. temperaturecooled
  4. extractionextracted with ethyl acetate (6×25 ml.)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. customevaporated in vacuo to a white solid which
  7. dissolutionwas dissolved in ethanol (3 ml.)
  8. additionadded to a solution of oxalic acid (0.071 g.) in ethanol (2 ml.)
  9. filtrationThe precipitated solid was filtered off
  10. washwashed with ethanol
  11. customdried at 50°/0.1 m

Sources & evidence

ORD record
ord-bdca32edbe2c47559017c808211cc2ef
Source dataset
uspto-grants-1980_12
Patent number
US04242350

Reaction notes

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