Sodium borohydride → HCID 18920285, compound

HRID 1975156Notes

Reaction equation

HRID 1975156 reaction equation
[BH4-].[Na+].[I-].[CH2:4]([O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][C:13]1[C:14]([C:18]2[CH:19]=[N+:20]([CH3:24])[CH:21]=[CH:22][CH:23]=2)=[N:15][S:16][N:17]=1)[CH3:5]>C(O)C>[CH2:4]([O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][C:13]1[C:14]([C:18]2[CH2:19][N:20]([CH3:24])[CH2:21][CH2:22][CH:23]=2)=[N:15][S:16][N:17]=1)[CH3:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 190753263-(4-(2-(2-Ethoxyethoxy)ethoxy)-1,2,5-thiadiazol-3-yl)-1-methylpyridinium iodide

Product 1

HCID 18920285HCID 18920285, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-10 °C

Procedure

Sodium borohydride (230 mg, 6 mmol) was added to a solution of 3-(4-(2-(2-ethoxyethoxy)ethoxy)-1,2,5-thiadiazol-3-yl)-1-methylpyridinium iodide (3 mmol) in ethanol (99.9%, 20 ml) and the reaction mixture was stirred at -10° C. for 1 h. After evaporation the residue was dissolved in water and extracted with ethyl acetate. The dried organic phases were evaporated and the residue purified by column chromatography (SiO2, eluent: ethyl acetate/methanol (4:1)). The title compound was crystallized as the oxalate salt from acetone to yield 290 mg. (M.p. 115°-116° C.; M+ : 313; Compound 43).

Workup

  1. customAfter evaporation the residue
  2. dissolutionwas dissolved in water
  3. extractionextracted with ethyl acetate
  4. customThe dried organic phases were evaporated
  5. customthe residue purified by column chromatography (SiO2, eluent: ethyl acetate/methanol (4:1))
  6. customThe title compound was crystallized as the oxalate salt from acetone
  7. customto yield 290 mg

Sources & evidence

ORD record
ord-c1311019a7714f4cac81dd9d2818539e
Source dataset
uspto-grants-1994_02
Patent number
US05284859

Reaction notes

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