Water → HCID 59674009, compound

HRID 1391473Notes

Reaction equation

HRID 1391473 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[S:11]([CH3:13])=[O:12].[N-:14]=[N+]=[N-].[Na+].S(=O)(=O)(O)O.O>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[S:11]([CH3:13])(=[NH:14])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 59674039HCID 59674039, compound

Product 1

HCID 59674009HCID 59674009, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.5 g (7.5 mmol) of (RS)-2-methyl-1-(methylsulfinyl)-4-nitrobenzene and 1.1 g (17.1 mmol) of sodium azide in 10.0 ml of CHCl3 are carefully mixed at 0° C. with 2.2 ml of concentrated sulfuric acid. The batch is heated first to room temperature and then to 45° C. while being stirred vigorously. It is stirred for 116 hours at this temperature. After cooling, it is mixed with water and extracted from DCM (2×). The aqueous phase is made basic with 2N NaOH solution and extracted from DCM. The combined organic phases are filtered through a Whatman filter and concentrated by evaporation. The crude product that is obtained is recrystallized from ethyl acetate. 1.3 g (6.1 mmol, corresponding to 81% of theory) of the product is obtained.

Workup

  1. stirringIt is stirred for 116 hours at this temperature
  2. temperatureAfter cooling
  3. extractionextracted from DCM (2×)
  4. extractionextracted from DCM
  5. filtrationThe combined organic phases are filtered through a Whatman
  6. filtrationfilter
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-0319f14855974c779ff19279adb98215
Source dataset
uspto-grants-2008_03
Patent number
US07338958B2

Reaction notes

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