Pyridine → 2-Methylsulfinyl-5-(1H-tetrazol-1-yl)benzoic Acid

HRID 637117Notes

Reaction equation

HRID 637117 reaction equation
[CH3:1][S:2][C:3]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[N:15][N:14]=[N:13]2)=[CH:8][C:4]=1[C:5]([OH:7])=[O:6].N1C=CC=CC=1.[Br-].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.S(=O)(O)[O-:57].[Na+]>O.O1CCCC1>[CH3:1][S:2]([C:3]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[N:15][N:14]=[N:13]2)=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])=[O:57]

Participants

7

Reactant 4

HCID 1049PyridineHCID 17977687Phenyltrimethylammonium bromide dibromideHCID 184645182-Methylthio-5-(1H-tetrazol-1-yl)benzoic AcidHCID 23665763Sodium Bisulfite

Product 1

HCID 184645052-Methylsulfinyl-5-(1H-tetrazol-1-yl)benzoic Acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Combine 2-methylthio-5-(1H-tetrazol-1-yl)benzoic acid (0.50 g, 2.0 mmol), pyridine (20 mL) and water (20 mL). Cool in an ice bath. Add phenyltrimethylammonium tribromide (0.75 g, 2 mmol) and tetrahydrofuran (20 mL). Warm to ambient temperature. After 1 hour, add a solution of sodium bisulfite (1 g) in water (1 mL). Extract the reaction mixture with ethyl acetate and then dichloromethane. Combine the organic layers, dry over MgSO4, filter, and evaporate in vacuo to give a residue. the title compound. Chromatograph the residue on silica gel eluting sequentially with ethyl acetate and then 10% methanol/ethyl acetate to give methyl 2-methylsulfinyl-5-(1H-tetrazol-1-yl)benzoate.

Workup

  1. temperatureCool in an ice bath
  2. extractionExtract the reaction mixture with ethyl acetate
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. customevaporate in vacuo
  6. customto give a residue

Sources & evidence

ORD record
ord-2b5e3cada9e041b4a625bad2d9d3e476
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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