Benzyl Alcohol → Benzyl azide

HRID 1816514Notes

Reaction equation

HRID 1816514 reaction equation
[CH2:1](O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C=O)C.[N-:14]=[N+:15]=[N-:16].[Na+].C(OCC)C>CN(C1C=CN=CC=1)C.O>[CH2:1]([N:14]=[N+:15]=[N-:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 33557Sodium Azide

Product 1

HCID 12152Benzyl azide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

2.07 ml of benzyl alcohol (20 mmole), 2.99 g of DMAP (1.2 eq) and 1.86 ml of MeSOCl2 (1.2 eq) were sequentially added to 25 ml of DMF. After stirring the mixture for 6 hours, 3.96 g of NaN3 (3 eq) was added thereto, and the mixture was stirred for 12 hours. The reaction mixture was treated with a mixture of diethyl ether and water, the ether extract was dried under MgSO4, ether was removed under a reduced pressure, and the resulting residue was subjected to column chromatography (silica gel 60, 230˜400 meshes, Merck) to obtain the title compound as a pale yellow liquid. The chromatography was conducted using a mixture of hexane and CH2Cl2 as an eluting solution whose mix ratio was gradually varied from 2:1 to 1:1 (v/v).

Workup

  1. stirringthe mixture was stirred for 12 hours
  2. extractionthe ether extract
  3. customwas dried under MgSO4
  4. customether was removed under a reduced pressure

Sources & evidence

ORD record
ord-61190ecd3a424a85b308dae5e448fd76
Source dataset
uspto-grants-2005_04
Patent number
US06884882B1

Reaction notes

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