Sodium Hydroxide → 3-[2-(2-Carbamoyl-3-methylguanidino)ethylthiomethyl]-5-guanidino-1,2,4-thiadiazole

HRID 1155776Notes

Reaction equation

HRID 1155776 reaction equation
[C:1]([N:3]=[C:4]([NH:19][CH3:20])[NH:5][CH2:6][CH2:7][S:8][CH2:9][C:10]1[N:14]=[C:13]([NH:15][C:16]([NH2:18])=[NH:17])[S:12][N:11]=1)#[N:2].[OH-:21].[Na+]>Cl>[C:1]([N:3]=[C:4]([NH:19][CH3:20])[NH:5][CH2:6][CH2:7][S:8][CH2:9][C:10]1[N:14]=[C:13]([NH:15][C:16]([NH2:18])=[NH:17])[S:12][N:11]=1)(=[O:21])[NH2:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178485071HCID 178485071, compound

Product 1

HCID 1784850813-[2-(2-Carbamoyl-3-methylguanidino)ethylthiomethyl]-5-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-[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; C9H17N9OS2.1.75 C2H2O4 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-a4c8ef92fb4e44bab68c1af376f96c05
Source dataset
uspto-grants-1982_06
Patent number
US04332949

Reaction notes

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