Sodium Azide → HCID 25013431, compound

HRID 455328Notes

Reaction equation

HRID 455328 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([C:15]3[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=3)[CH2:14][O:13]2)=[CH:8][CH:7]=1>CC(C)=O.O>[N:1]([CH2:14][C:12]([C:9]1[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=1)([C:15]1[CH:16]=[CH:17][C:18]([I:21])=[CH:19][CH:20]=1)[OH:13])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 593172172-(4-Chlorophenyl)-2-(4-iodophenyl)oxirane

Product 1

HCID 25013431HCID 25013431, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

Sodium azide (13.86 g, 213.2 mmol) was added to a mixture of (RS)-2-(4-chlorophenyl)-2-(4-iodophenyl)oxirane (50.66 g, 142.1 mmol) in acetone (400 ml) and water (40 ml) and the mixture was stirred and held at reflux for 4 days. Upon cooling to room temperature the acetone was removed in vacuo, the residue was dissolved in ethyl acetate (500 ml), washed with water (250 ml) and then with brine (250 ml), the organic layer was separated and the solvent removed in vacuo to afford (RS)-2-azido-1-(4-chlorophenyl)-1-(4-iodophenyl)ethanol (56.77 g, 100%) as a pale yellow oil that slowly solidified upon standing to afford an off-white solid. 1H NMR (DMSO-d6) 7.68 (2H, d), 7.44 (2H, d), 7.38 (2H, d), 7.24 (2H, d), 6.38 (1H, br s), 3.99 (2H, s). MS: [M−H]− 398.

Workup

  1. temperatureat reflux for 4 days
  2. customwas removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate (500 ml)
  4. washwashed with water (250 ml)
  5. customwith brine (250 ml), the organic layer was separated
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-f8890bd11bcb45ae9d20afe7d5e4c015
Source dataset
uspto-grants-2013_07
Patent number
US08497294B2

Reaction notes

Loading…