HCID 10198942, compound → HCID 15888357, compound

HRID 2289600Notes

Reaction equation

HRID 2289600 reaction equation
Br[C:2]1[N:9]2[C:5](=[N:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)[S:4][N:3]=1.[CH3:14][O-:15].[Na+]>CO>[CH3:14][O:15][C:2]1[N:9]2[C:5](=[N:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=32)[S:4][N:3]=1

Participants

4

Reactant 2

HCID 10198942HCID 10198942, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 15888357HCID 15888357, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cooled mixture of 3-bromo-1,2,4-thiadiazolo[4,5-a]benzimidazole (4.55 g, 17.9 mmole) in 50 mL of methanol, sodium methoxide (0.967 g, 17.9 mmole) was added in one portion and stirred for 4 h at room temperature. The reaction mixture was evaporated to dryness under vacuum and the residue was taken-up in ethyl acetate and washed with water. The organic layer was dried with sodium sulfate, filtered and evaporated to yield 3.64 g (94%) of 3-methoxy-1,2,4-thiadiazolo[4,5-a]benzimidazole as colourless crystals: mp 172-175° C.; 1H NMR (CDCl3) δ 7.83 (d, 1H), 7.75 (d, 1H), 7.42 (t, 1H), 7.27 (t, 1H), 4.32 (s, 3H) ppm; 13C NMR (CDCl3) δ 163.2, 150.3, 148.1, 128.119.2, 111.7, 57.5119.2, 111.7, 57.5 ppm; IR (KBr) ν 3418, 2942, 1595, 1492, 1404, 1275, 1255, 1206, 1083, 755 cm-1. Anal. Calcd for C9H7N3OS: C, 52.67; H, 3.44; N, 20.49. Found: C, 52.28; H, 3.36; N, 20.45.

Workup

  1. additionwas added in one portion
  2. customThe reaction mixture was evaporated to dryness under vacuum
  3. washwashed with water
  4. dry with materialThe organic layer was dried with sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-36ffea0875b44feba4d5e1972da19ba7
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

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