Hydrochloric Acid → HCID 178527985, compound

HRID 386390

Reaction equation

HRID 386390 reaction equation
[C:1]1([N:11]=[C:12]=[S:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[N-:14]=[N+:15]=[N-:16].[Na+].Cl>C(O)C>[C:1]1([N:11]2[C:12]([SH:13])=[N:16][N:15]=[N:14]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 110801-Naphthyl IsothiocyanateHCID 33557Sodium Azide

Product 1

HCID 178527985HCID 178527985, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
79 °C

Procedure

To a solution of 1-naphthalenylisothiocyanate (500 mg, 2.7 mmol) in ethanol (150 mL) was added sodium azide (2.8 g, 43 mmol) and the mixture was heated to 79° C. for 2 hours. The reaction mixture was then cooled to room temperature, aqueous HCl solution (12N, 1.5 mL) added and the mixture concentrated. The resulting residue was diluted with ethyl acetate and extracted with aqueous NaOH solution (1N) and the aqueous layer acidified with aqueous HCl solution (12N) until a precipitate formed. The precipitate was collected and used in the next step without further purification (520 mg, 85% yield).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. concentrationthe mixture concentrated
  3. additionThe resulting residue was diluted with ethyl acetate
  4. extractionextracted with aqueous NaOH solution (1N)
  5. customformed
  6. customThe precipitate was collected
  7. customused in the next step without further purification (520 mg, 85% yield)

Sources & evidence

ORD record
ord-c8da1addf57740abb8024f26521d5f0c
Source dataset
uspto-grants-2013_02
Patent number
US08372807B2

Linked notes

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