Water → HCID 20505518, compound

HRID 355244Notes

Reaction equation

HRID 355244 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].O.CS(O[CH:11]([CH3:16])[CH2:12][CH2:13][C:14]#[N:15])(=O)=O>C(O)C>[N:1]([CH:11]([CH3:16])[CH2:12][CH2:13][C:14]#[N:15])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 20505450HCID 20505450, compound

Product 1

HCID 20505518HCID 20505518, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of NaN3 (15 g) in boiling water (20 ml) was added a solution of crude 4-methanesulphonyloxypentanonitrile (37.7 g, ≈0.189 mol) in ethanol (240 ml) and the mixture refluxed for 1.5 h. After cooling the mixture was partitioned between H2O and CH2Cl2. The organic phase was dried and concentrated in vacuo to give 21.4 g of the title material as a light brown oil, (91.6): 1Hmr (CDCl3) δ: 4.05 (1H, q, J=13 Hz), 2.46 (2H, t, J=13 Hz), 1.8 (2H, t, J=13 Hz) and 1.35 ppm (3H, d, J=13 Hz); ir (neat) νmax : 2242, 2100 cm-1.

Workup

  1. temperaturethe mixture refluxed for 1.5 h
  2. temperatureAfter cooling the mixture
  3. customwas partitioned between H2O and CH2Cl2
  4. customThe organic phase was dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5542a75ab32e4b53b585476c5848c3d4
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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