Hydrochloric Acid → HCID 178448769, compound

HRID 1656885Notes

Reaction equation

HRID 1656885 reaction equation
[C:1]([N:5]=[C:6]=[S:7])([CH3:4])([CH3:3])[CH3:2].[N-:8]=[N+:9]=[N-:10].[Na+].Cl>C(O)C.O>[C:1]([N:5]1[C:6](=[S:7])[NH:10][N:9]=[N:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11544tert-Butyl isothiocyanateHCID 33557Sodium Azide

Product 1

HCID 178448769HCID 178448769, compoundYield 30.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Combined solutions of 50.0 g (0.435 mol) tert-butyl isothiocyanate in 125 ml ethanol and 56.6 g (0.850 mol) sodium azide in 900 ml water were heated under reflux with stirring for 5.5 hours. After cooling, the solution was acidified to pH 1 with hydrochloric acid and extracted with ether. The extracts were washed with water and aqueous saturated sodium chloride solution, dried over magnesium sulfate, and evaporated to yield 21 g of colorless oil which later crystallized. The product of a repeat of this preparation was triturated with ligroine to yield colorless crystals of Ia mp 92°-94°, confirmed by NMR, infrared, and mass spectral data as well as elemental analysis.

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling
  3. extractionextracted with ether
  4. washThe extracts were washed with water and aqueous saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-f2cddb51456c4a3ab2076d8fee34ff96
Source dataset
uspto-grants-1993_10
Patent number
US05256523

Reaction notes

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