Sodium Azide → 2-Azidomethyl-3-phenylbenzo[b]thiophene

HRID 242859Notes

Reaction equation

HRID 242859 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]1([C:11]2[C:12]3[CH:25]=[CH:24][CH:23]=[CH:22][C:13]=3[S:14][C:15]=2[CH2:16]OS(C)(=O)=O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CN(C=O)C.O>[N:1]([CH2:16][C:15]1[S:14][C:13]2[CH:22]=[CH:23][CH:24]=[CH:25][C:12]=2[C:11]=1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86668872(3-Phenylbenzo[b]thiophen-2-yl)methyl methanesulfonate

Product 1

HCID 866688732-Azidomethyl-3-phenylbenzo[b]thiopheneYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium azide (179 mg, 2.76 mmol) was added to a solution of methanesulfonic acid 3-phenylbenzo[b]thiophen-2-ylmethyl ester (828 mg, 1.84 mmol) in DMF (10 mL) and the mixture was stirred at RT for 18 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was washed with brine, then dried (Na2SO4) and concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-35% DCM in cyclohexane) affording 2-azidomethyl-3-phenylbenzo[b]thiophene as a clear oil (244 mg, 50%). LCMS: RT 4.46 min [M+H-N2]+ 237.8.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customthe resulting residue was purified by column chromatography (Si—PCC, gradient 0-35% DCM in cyclohexane)

Sources & evidence

ORD record
ord-ff4f546fd7904f3b988cb0d5783279b6
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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