Sulfuric Acid → HCID 117666880, compound

HRID 712781Notes

Reaction equation

HRID 712781 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8][S:9]([CH3:11])=[O:10])[CH:7]=1.[N-:12]=[N+]=[N-].[Na+].OS(O)(=O)=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8][S:9](=[NH:12])([CH3:11])=[O:10])[CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 117667333HCID 117667333, compound

Product 1

HCID 117666880HCID 117666880, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

3-Bromo-5-methanesulfinylmethyl-pyridine (3.0 g, 13 mmol) is dissolved in chloroform (100 mL) and the solution is cooled to 0° C. Sodium azide (1.3 g, 21 mmol) is added and the reaction mixture is stirred for 5 minutes. Then concentrated H2SO4 (10 mL) is slowly added at 0° C. and then the mixture is heated up to 50° C. for 16 hrs. After cooling down to room temperature, ice cold water is added and the mixture is extracted with CH2Cl2. The aqueous layer is separated, basified with saturated Na2CO3 solution and extracted with more CH2Cl2. Organic layers are combined, dried over anhydrous Na2SO4 and concentrated to give the crude product. Purification by flash column chromatography affords 1.6 g of 3-bromo-5-[imino(methyl)oxo-λ6-sulfanyl]methyl-pyridine.

Workup

  1. temperaturethe mixture is heated up to 50° C. for 16 hrs
  2. temperatureAfter cooling down to room temperature
  3. additionice cold water is added
  4. extractionthe mixture is extracted with CH2Cl2
  5. customThe aqueous layer is separated
  6. extractionextracted with more CH2Cl2
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customto give the crude product
  10. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-e393f524731a4e9d8e9e4c478b12bd2b
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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