Sodium Azide → HCID 21070649, compound

HRID 1371769Notes

Reaction equation

HRID 1371769 reaction equation
Br[CH:2]1[CH2:7][CH2:6][N:5]([S:8]([CH3:11])(=[O:10])=[O:9])[CH2:4][CH:3]1[OH:12].[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C)C=O>[N:13]([CH:2]1[CH2:7][CH2:6][N:5]([S:8]([CH3:11])(=[O:10])=[O:9])[CH2:4][CH:3]1[OH:12])=[N+:14]=[N-:15]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 13042967HCID 13042967, compound

Product 1

HCID 21070649HCID 21070649, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
84 °C

Procedure

To a stirred solution of the bromide (70 mg, 0.27 mmol, Example 307) in dimethylformamide (3 mL), sodium azide (80 mg, 1.23 mmol) was added and the mixture was stirred at 84° C. overnight. The solvent was removed and the residue was chromatographed (50% ethyl acetate/hexane) to give the desired product as a colorless oil. 51 mg, 86%. H1NMR (300 MHz, CDCl3), ppm: 1.60–1.70 (m), 1H; 2.05–2.20(m), 1H; 2.80–3.05 (m), 2H; 2.83 (s), 3H; 3.10 (br), 1H (OH); 3.40–3.51 (m), 1H; 3.51–3.62 (m), 1H. 3.65–3.80 (m), 2H.

Workup

  1. customThe solvent was removed
  2. customthe residue was chromatographed (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c3128b2d1deb472ea1193dcfc311ff7b
Source dataset
uspto-grants-2007_01
Patent number
US07157455B2

Reaction notes

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