Sulfuric Acid → HCID 86730870, compound

HRID 589276Notes

Reaction equation

HRID 589276 reaction equation
[CH3:1][N+:2]1[C:6]([S-:7])=[N:5][N:4]([CH:8]([CH3:11])[CH2:9][CH3:10])[N:3]=1.S(=O)(=O)(O)O.[OH-].[Na+].C(=O)(O)[O-].[Na+].[F:24][B-:25]([F:28])([F:27])[F:26].[Na+]>O>[F:24][B-:25]([F:28])([F:27])[F:26].[CH3:1][N+:2]1[C:6]([S:7][CH:8]([CH3:11])[CH2:9][CH3:10])=[N:5][N:4]([CH:8]([CH3:11])[CH2:9][CH3:10])[N:3]=1

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 516892Sodium Bicarbonate2×HCID 4343483Sodium TetrafluoroborateHCID 86730872HCID 86730872, compound

Product 1

HCID 86730870HCID 86730870, compoundYield 150%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-methyl-3-(1-methylpropyl)tetrazolium-5-thiolate (173.7 mg, 1.0 mmol) was introduced into a recovery flask; concentrated sulfuric acid (1.7 mL) and C2H5(CH3)CHOH (s-BuOH, 92.0 μL, 1.0 mmol) were added to this; and stirring was performed for 13 hours. Then, while on an ice bath, an aqueous sodium hydroxide solution (30.0 mmol, 10 mL) and aqueous sodium bicarbonate (30.0 mmol, 10.0 mL) were added dropwise using a dropping funnel. More aqueous sodium bicarbonate was added to bring to neutrality (pH=6-7). Extraction with methylene chloride, washing with an aqueous sodium carbonate solution, drying over anhydrous sodium sulfate, and distillation of the solvent yielded a yellow liquid. On the other hand, sodium fluoroborate (165.0 mg, 1.5 mmol) was added to the water layer followed by extraction with methylene chloride, drying over anhydrous sodium sulfate, and removal of the solvent by distillation to obtain 1-methyl-3-(1-methylpropyl)-5-(1-methylpropylthio)tetrazolium tetrafluoroborate (yield=237.1 mg, 75%).

Workup

  1. extractionExtraction with methylene chloride
  2. washwashing with an aqueous sodium carbonate solution
  3. dry with materialdrying over anhydrous sodium sulfate, and distillation of the solvent
  4. customyielded a yellow liquid
  5. extractionfollowed by extraction with methylene chloride
  6. dry with materialdrying over anhydrous sodium sulfate, and removal of the solvent by distillation

Sources & evidence

ORD record
ord-328d2ad22e594efe985145af588a178f
Source dataset
uspto-grants-2016_01
Patent number
US09231278B2

Reaction notes

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