Imidazole → 1H-Imidazole-1-sulfonyl azide hydrochloride

HRID 1912103Notes

Reaction equation

HRID 1912103 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].C(#N)C.[S:8](Cl)([Cl:11])(=[O:10])=[O:9].[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1>C(OCC)(=O)C>[ClH:11].[N:13]1([S:8]([N:1]=[N+:2]=[N-:3])(=[O:10])=[O:9])[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6342AcetonitrileHCID 24648Sulfuryl chlorideHCID 33557Sodium Azide

Product 1

HCID 235839821H-Imidazole-1-sulfonyl azide hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sodium azide (13.0 g) and acetonitrile (200 mL) were mixed. To the mixture was added dropwise sulfuryl chloride (16.1 mL) at ice temperature. The mixture was stirred at RT overnight, and then to the mixture was added imidazole (25.9 g) at ice temperature. The mixture was stirred at RT for 4 hr, and then to the mixture was added ethyl acetate. The mixture was washed with water (400 mL×2) and saturated aqueous sodium bicarbonate (400 mL×2), then dried over magnesium sulfate. The magnesium sulfate was filtered off. To the filtrate was added a solution of hydrochloric acid in ethyl acetate at ice temperature. The precipitated solid was collected on a filter to give the title compound (27.7 g).

Workup

  1. stirringThe mixture was stirred at RT for 4 hr
  2. washThe mixture was washed with water (400 mL×2) and saturated aqueous sodium bicarbonate (400 mL×2)
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. additionTo the filtrate was added a solution of hydrochloric acid in ethyl acetate at ice temperature
  6. customThe precipitated solid was collected on
  7. filtrationa filter

Sources & evidence

ORD record
ord-fe2ee63ee0fc4e30a77bf4591199f23f
Source dataset
uspto-grants-2013_12
Patent number
US08604069B2

Reaction notes

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