Sodium Azide → HCID 178505919, compound

HRID 1193602Notes

Reaction equation

HRID 1193602 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][N:12]=[C:13]=[S:14])[CH:5]=[C:6]([F:8])[CH:7]=1.[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C)C=O.O>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][N:12]2[C:13]([SH:14])=[N:17][N:16]=[N:15]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 140499143-(3,5-Difluorophenyl)propyl Isothiocyanate

Product 1

HCID 178505919HCID 178505919, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(3,5-difluorophenyl)propyl isothiocyanate (0.0177 mol) in dimethylformamide (35 ml) was added water (12 ml), followed by sodium azide (0.0361 mol). The reaction was stirred one hour, then it was diluted with water and washed with ethyl acetate. The aqueous phase was acidified with 3N aqueous hydrogen chloride, extracted into ethyl acetate, washed with water, dried over sodium sulfate and was concentrated. The residue was dissolved in ethyl ether and dicyclohexylamine (1.9 ml) was added. The resulting salt was filtered and partitioned, with stirring, between ethyl ether and 3N aqueous hydrogen chloride. The ethereal layer was washed with water, dried over sodium sulfate and concentrated. The crude product was recrystallized from pet. ether to yield 1.2 g (27%) white crystals: mp 80°-81° (pet. ether).

Workup

  1. washwashed with ethyl acetate
  2. extractionextracted into ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationwas concentrated
  6. dissolutionThe residue was dissolved in ethyl ether
  7. additiondicyclohexylamine (1.9 ml) was added
  8. filtrationThe resulting salt was filtered
  9. custompartitioned
  10. stirringwith stirring, between ethyl ether and 3N aqueous hydrogen chloride
  11. washThe ethereal layer was washed with water
  12. dry with materialdried over sodium sulfate
  13. concentrationconcentrated
  14. customThe crude product was recrystallized from pet. ether

Sources & evidence

ORD record
ord-95ca88c3e79d433db3fe80b009f38773
Source dataset
uspto-grants-1989_03
Patent number
US04810811

Reaction notes

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