Dimethyl Sulfoxide → 4-(Benzoxazol-2-yl)benzylazide

HRID 863854Notes

Reaction equation

HRID 863854 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1.[N-:18]=[N+:19]=[N-:20].[Na+].CS(C)=O>C1COCC1.C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:18]=[N+:19]=[N-:20])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 110335154-(Benzoxazol-2-yl)benzyl bromide

Product 1

HCID 194207644-(Benzoxazol-2-yl)benzylazide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(benzoxazol-2-yl)benzyl bromide (0.49 g; 1.7 mmol) in THF (3 ml) is added sodium azide (0.22 g; 3.4 mmol) and dimethylsulfoxide (1 ml). The reaction is stirred for 24 hours and diluted with CH2Cl2, washed with H2O 3× and brine, dried (MgSO4) and concentrated in vacuo. The product is purified by column chromatography using 50% CH2Cl2 /petroleum ether to yield 4-(benzoxazol-2-yl)benzylazide as a white solid which is used directly in Step B.

Workup

  1. washwashed with H2O 3× and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by column chromatography

Sources & evidence

ORD record
ord-38742b561f6e4be1b1432ea6d6947dd8
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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