Sodium borohydride → HCID 18920258, compound

HRID 1975130Notes

Reaction equation

HRID 1975130 reaction equation
[BH4-].[Na+].[I-].[CH3:4][C:5]([CH3:21])=[CH:6][CH2:7][O:8][C:9]1[C:10]([C:14]2[CH:15]=[N+:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)=[N:11][S:12][N:13]=1>C(O)C>[CH3:4][C:5]([CH3:21])=[CH:6][CH2:7][O:8][C:9]1[C:10]([C:14]2[CH2:15][N:16]([CH3:20])[CH2:17][CH2:18][CH:19]=2)=[N:11][S:12][N:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 190753893-(3-(3-Methyl-2-butenyloxy)-1,2,5-thiadiazol-4-yl)-1-methylpyridinium iodide

Product 1

HCID 18920258HCID 18920258, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-10 °C

Procedure

Sodium borohydride (220 mg, 6 mmol) was added to a solution of 3-(4-(3-methyl-2-butenyloxy)-1,2,5-thiadiazol-3-yl)-1-methylpyridinium iodide (0.92 g, 2.3 mmol) in ethanol (99.9%, 15 ml) and the reaction mixture was stirred at -10° C. for 0.5 h. After evaporation the residue was dissolved solved in water and extracted with ethyl acetate. The dried organic phases were evaporated and the residue purified by column chromatography (Si02, eluent: ethyl acetate/methanol (4:1)). The title compound was crystallized as the oxalate salt from acetone to yield 380 mg. (M.p. 150°-151° C.; M+ : 265; Compound 27).

Workup

  1. customAfter evaporation the residue
  2. dissolutionwas dissolved
  3. extractionextracted with ethyl acetate
  4. customThe dried organic phases were evaporated
  5. customthe residue purified by column chromatography (Si02, eluent: ethyl acetate/methanol (4:1))
  6. customThe title compound was crystallized as the oxalate salt from acetone
  7. customto yield 380 mg

Sources & evidence

ORD record
ord-ff463001b0e9491fa1c128e976728743
Source dataset
uspto-grants-1994_02
Patent number
US05284859

Reaction notes

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