Water → HCID 178419937, compound

HRID 619350Notes

Reaction equation

HRID 619350 reaction equation
[C:1]1([CH2:11][C:12]#[N:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+].[N-:16]=[N+:17]=[N-:18].[Na+].O>CN(C=O)C>[C:1]1([CH2:11][C:12]2[NH:18][N:17]=[N:16][N:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 85961-NaphthaleneacetonitrileHCID 25517Ammonium ChlorideHCID 33557Sodium Azide

Product 1

HCID 178419937HCID 178419937, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of the above acetonitrile (5.40 g, 32 mmol), ammonium chloride (2.59 g, 48 mmol) and sodium azide (3.15 g, 48 mmol) in N,N'-dimethylformamide (100 ml) was stirred at 125° C. for 16 hours. After cooling the mixture was poured into water (300 ml) and extracted with ethyl acetate (2×150 ml) The combined organic phases were washed with water (100 ml) and evaporated in vacuo. The residue was crystallised from diethyl ether (20 ml), filtered off and washed with diethyl ether affording 1.86 g (27%) of the title compound as a solid.

Workup

  1. temperatureAfter cooling the mixture
  2. extractionextracted with ethyl acetate (2×150 ml) The combined organic phases
  3. washwere washed with water (100 ml)
  4. customevaporated in vacuo
  5. customThe residue was crystallised from diethyl ether (20 ml)
  6. filtrationfiltered off
  7. washwashed with diethyl ether affording 1.86 g (27%) of the title compound as a solid

Sources & evidence

ORD record
ord-562e77285c9b4f8c81b0da662b8f4748
Source dataset
uspto-grants-1999_09
Patent number
US05958957

Reaction notes

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