Sodium Azide → HCID 21925012, compound

HRID 1107721Notes

Reaction equation

HRID 1107721 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9]O)[CH:5]=[CH:6][CH:7]=1.CC1C=CC(S([O-])(=O)=O)=CC=1.[N-:22]=[N+:23]=[N-:24].[Na+]>CS(C)=O.O>[N:22]([CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)=[N+:23]=[N-:24]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 131721806HCID 131721806, compound

Product 1

HCID 21925012HCID 21925012, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A mixture of 3-bromobenzeneethanol 4-methylbenzenesulphonate [Example H(b)] (3.96 g, 11.2 mmol) and sodium azide (22.4 mmol, 1.46 g) in DMSO (50 ml) was stirred at room temperature for 16 h, diluted with water (200 ml), extracted with diethyl ether (2×40 ml), the combined extracts washed with saturated aqueous sodium chloride (40 ml), dried over sodium sulphate and evaporated, to give the product as a pale yellow oil (2.46 g). M+ 227; 360 MHz 1H n.m.r (CDCl3) 7.52 (1H, s), 7.45-7.42 (1H, m), 7.31-7.25 (2H, m), 3.58 (2H, t, 7.0 Hz), 2.85 (2H, t, J 7.0 Hz).

Workup

  1. extractionextracted with diethyl ether (2×40 ml)
  2. washthe combined extracts washed with saturated aqueous sodium chloride (40 ml)
  3. dry with materialdried over sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-b4695938f1a84ec1ada7f685d6112b2d
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Reaction notes

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