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

HRID 242887Notes

Reaction equation

HRID 242887 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 stirred at RT for 18 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic fraction was washed with brine, dried (Na2SO4) and concentrated in vacuo and the resulting residue purified by column chromatography (Si—PCC, gradient 0-35% DCM in cyclohexane) affording the title compound as a clear oil (244 mg, 50%). LCMS (Method C): RT 4.46 min [M+H-N2]+ 237.8

Workup

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

Sources & evidence

ORD record
ord-995ee78e559d4364893087bdd001e8ad
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…