Sodium Azide → HCID 20505601, compound

HRID 355268Notes

Reaction equation

HRID 355268 reaction equation
S(O[CH:12]([CH2:21][CH3:22])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])(C1C=CC(C)=CC=1)(=O)=O.[N-:23]=[N+:24]=[N-:25].[Na+]>CS(C)=O>[N:23]([CH:12]([CH2:21][CH3:22])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[N+:24]=[N-:25]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 20505538HCID 20505538, compound

Product 1

HCID 20505601HCID 20505601, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

t-Butyl 3-tosyloxypentanoate (7.75 g, 23.6 mmol) was added to a suspension of sodium azide (3.07 g, 47.2 mmol) in dry DMSO (135 ml) and stirred at room temperature for 66 h. The reaction mixture was poured into ice-water (200 ml) and extracted with CH2Cl2 (2×150 ml). The organic extracts were combined, washed with water (4×150 ml) and dried over anhydrous MgSO4. Evaporation of the CH2Cl2 under reduced pressure gave an oil (4.18 g, 89.4%). ir (neat) νmax : 2096 (N3) and 1720 cm-1 (C=O of ester); 1Hmr (CDCl3) δ: 1.0 (3H, t), 1.27-1.85 (2H, m), 1.48 (9H, s), 2.40 (2H, d) and 3.68 ppm (H, m).

Workup

  1. extractionextracted with CH2Cl2 (2×150 ml)
  2. washwashed with water (4×150 ml)
  3. dry with materialdried over anhydrous MgSO4
  4. customEvaporation of the CH2Cl2 under reduced pressure

Sources & evidence

ORD record
ord-e60254698a7844ab89d46c45d5b33dbe
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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