Diisopropylethylamine → 1-phenyl-1H-1,2,3-triazole-5-carbonitrile

HRID 1506625Notes

Reaction equation

HRID 1506625 reaction equation
[C:1]1([N:7]2[C:11]([C:12]([NH2:14])=O)=[CH:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.CS(OS(C)(=O)=O)(=O)=O>ClCCl>[C:1]1([N:7]2[C:11]([C:12]#[N:14])=[CH:10][N:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 81560Methanesulfonic anhydrideHCID 184741521-phenyl-1H-1,2,3-triazole-5-carboxamide

Product 1

HCID 846537091-phenyl-1H-1,2,3-triazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 9B (crude product) and DIPEA (1.5 mL, 8.4 mmol) in dichloromethane (10 mL), methanesulfonic anhydride (1.17, 6.7 mmol) was added to the mixture. Then it was stirred for overnight. The organic layer was washed with brine twice. The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was purified by flash column (Rf: 0.6, 15% EtOAc/Hexanes) to provide the desired product. MS (m/z) 171 [M+H]+.

Workup

  1. washThe organic layer was washed with brine twice
  2. dry with materialThe organic layer was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash column (Rf: 0.6, 15% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-7d754972e2d64fdf9e3c9874335763bf
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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