Sodium Chloride → HCID 15888356, compound

HRID 1953146Notes

Reaction equation

HRID 1953146 reaction equation
Br[C:2](Br)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:3]1[N:10]2[C:6](=[N:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[S:5][N:4]=1.C(=O)(O)[O-:23].[Na+].[Cl-].[Na+]>O1CCCC1.O.[N+]([O-])([O-])=O.[Ag+]>[O:23]=[C:2]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:3]1[N:10]2[C:6](=[N:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=32)[S:5][N:4]=1

Participants

7

Reactant 3

HCID 5234Sodium ChlorideHCID 516892Sodium BicarbonateHCID 23303055HCID 23303055, compound

Product 1

HCID 15888356HCID 15888356, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[dibromo(2-pyridyl)methyl]-1,2,4-thiadiazolo[4,5-a]benzimidazole (2.02 g, 4.76 mmol) in 75 mL tetrahydrofuran was added a solution of silver nitrate (0.890 g, 5.24 mmol) in 75 mL water. The suspension was stirred for 2 days and then basified to pH 6 with aqueous sodium bicarbonate. After the addition of 1 mL saturated aqueous sodium chloride, the mixture was filtered on celite and the celite was washed with ethyl acetate. After extraction with water, the ethyl acetate was dried and evaporated to give a crude residue which was purified by flash chromatography using a mixture of chloroform/methanol 10:0.1 as the eluent. 1.05 g (78%) of the title compound was obtained as a yellow solid: mp 182-186° C. (dec); 1H NMR (CDCl3)δ 8.85 (m, 1H), 8.31 (dt, 1H), 8.19 (d, 1H), 8.01 (td, 1H), 7.83 (d, 1H), 7.63 (ddd, 1H), 7.50 (ddd, 1H), 7.35 (ddd, 1H) ppm; IR (film) 1673, 1511, 1444, 1235, 1057, 879, 733 cm-1 ; MS m/z 280 (M+), 148 (M+ -(2-pyridyl)C(O)CN).

Workup

  1. filtrationthe mixture was filtered on celite
  2. washthe celite was washed with ethyl acetate
  3. extractionAfter extraction with water
  4. dry with materialthe ethyl acetate was dried
  5. customevaporated
  6. customto give a crude residue which
  7. customwas purified by flash chromatography
  8. additiona mixture of chloroform/methanol 10:0.1 as the eluent

Sources & evidence

ORD record
ord-11daf3ac8e4e440ca92ddb3d5713fa56
Source dataset
uspto-grants-2000_09
Patent number
US06114537

Reaction notes

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