Hydrochloric Acid → HCID 178512713, compound

HRID 1758667Notes

Reaction equation

HRID 1758667 reaction equation
[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH2:14])[N:9]=1)[C:2]([NH2:4])=[NH:3].C[O:16][C:17]1[C:21](OC)=[N:20][S:19](=[O:24])[N:18]=1.[OH-].[Na+].Cl>CO>[NH:1]([C:5]1[S:6][CH:7]=[C:8]([CH2:10][S:11][CH2:12][CH2:13][NH:14][C:21]2[C:17]([OH:16])=[N:18][S:19](=[O:24])[N:20]=2)[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxideHCID 1785127232-[4-(2-Aminoethylsulfanylmethyl)-1,3-thiazol-2-yl]guanidine

Product 1

HCID 178512713HCID 178512713, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine (4.15 g; 17.9 mmoles) in 50 ml of methanol was added dropwise over a 30 minute period to a solution of 3,4-dimethoxy-1,2,5-thiadiazole 1-oxide (2.91 g; 17.9 mmoles) in 350 ml of methanol that had been cooled in an ice-water bath. The reaction mixture was treated with a solution of sodium hydroxide pellets (3.58 g; 89.5 mmoles) in methanol. After stirring overnight at ambient temperature, the mixture was neutralized with 14.9 ml (89.5 mmoles) of aqueous 6.0 N HCl and after 10 minutes was evaporated under reduced pressure. The solid residue was triturated for 2 hours with 70 ml of water at ambient temperature and filtered to give product. Recrystallization from water yielded the title compound, mp 148°-151°.

Workup

  1. temperaturehad been cooled in an ice-water bath
  2. customwas evaporated under reduced pressure
  3. customThe solid residue was triturated for 2 hours with 70 ml of water at ambient temperature
  4. filtrationfiltered
  5. customto give product
  6. customRecrystallization from water

Sources & evidence

ORD record
ord-a3d38483c7fc45dcb2f2f60604954332
Source dataset
uspto-grants-1983_02
Patent number
US04374248

Reaction notes

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