Hydrochloric Acid → HCID 178512713, compound

HRID 1980721Notes

Reaction equation

HRID 1980721 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 dropwioe 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 6.0N 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-1fccfc12dcb24d79ad6482fb9e82bcd1
Source dataset
uspto-grants-1985_04
Patent number
US04510309

Reaction notes

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