Sodium Methoxide → HCID 178512709, compound

HRID 1702406Notes

Reaction equation

HRID 1702406 reaction equation
C[O-].[Na+].Cl.Cl.[NH:6]([C:10]1[S:11][CH:12]=[C:13]([CH2:15][S:16][CH2:17][CH2:18][NH2:19])[N:14]=1)[C:7]([NH2:9])=[NH:8].CO[C:22]1[C:26](OC)=[N:25][S:24](=[O:29])[N:23]=1>CO>[NH:6]([C:10]1[S:11][CH:12]=[C:13]([CH2:15][S:16][CH2:17][CH2:18][NH:19][C:22]2[C:26]([NH:19][CH2:18][CH2:17][S:16][CH2:15][C:13]3[N:14]=[C:10]([NH:6][C:7]([NH2:9])=[NH:8])[S:11][CH:12]=3)=[N:25][S:24](=[O:29])[N:23]=2)[N:14]=1)[C:7]([NH2:9])=[NH:8]

Participants

5

Reactant 3

HCID 10942334Sodium MethoxideHCID 129139473,4-Dimethoxy-1,2,5-thiadiazole 1-oxideHCID 178478806HCID 178478806, compound

Product 1

HCID 178512709HCID 178512709, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium methoxide (2.16 g; 40.0 mmoles) in 100 ml of CH3OH that was cooled to 0° in an ice-water bath was added 2-[(2-guanidinothiazol-4-yl)methylthio]ethylamine dihydrochloride (6.09 g; 20.0 mmoles) and, after 20 minutes of stirring, the solution was treated with 3,4-dimethoxy-1,2,5-thiadiazole 1-oxide (1.62 g; 10 mmoles). The reaction mixture was stirred at ambient temperature for 65 hours and evaporated under reduced pressure. The residue was chromatographed on 100 g of silica gel (230-400 mesh) by flash chromatography using a gradient elution of acetonitrile-methanol. The appropriate fractions were combined, evaporated and the residue chromatographed on a Preparative HPLC system using μ-porasil silica gel. The appropriate fractions were combined, and evaporated under reduced pressure to give the title compound as an amorphous solid; the NMR spectrum (100 MHz) in d6 dimethyl sulfoxide showed the presence of approximately 0.11 mole of ethanol.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 65 hours
  2. customevaporated under reduced pressure
  3. customThe residue was chromatographed on 100 g of silica gel (230-400 mesh) by flash chromatography
  4. washa gradient elution of acetonitrile-methanol
  5. customevaporated
  6. customthe residue chromatographed on a Preparative HPLC system
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1c0a22a14ddf444a947e82b6578fbe9a
Source dataset
uspto-grants-1983_04
Patent number
US04380639

Reaction notes

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