Triethylamine → HCID 89619101, compound

HRID 1502060Notes

Reaction equation

HRID 1502060 reaction equation
[CH3:1][C:2]1[C:10]2[C:6](=[N:7][O:8][N:9]=2)[CH:5]=[CH:4][C:3]=1[OH:11].[O:12](S(C(F)(F)F)(=O)=O)[S:13]([C:16]([F:19])([F:18])[F:17])(=O)=[O:14].CCN(CC)CC>C(Cl)Cl>[F:17][C:16]([F:19])([F:18])[S:13]([O:11][C:3]1[CH:4]=[CH:5][C:6]2=[N:7][O:8][N:9]=[C:10]2[C:2]=1[CH3:1])(=[O:14])=[O:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 136635333HCID 136635333, compound

Product 1

HCID 89619101HCID 89619101, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methyl-2,1,3-benzoxadiazol-5-ol (2.10 g, 17.9 mmol) in 40 mL of dry DCM was added Tf2O (7.61 g, 26.9 mmol) dropwise at −78° C. under Ar and stirred for 5 minutes, then Et3N (2.73 g, 26.9 mmol) was added dropwise to the mixture and the reaction was stirred at 0° C. for 4 hours. Then the reaction was poured into 200 mL of ice water and extracted with DCM (50 mL×3). The combined organic layers were washed with brine, dried and concentrated, the residue was purified by silica gel column to give the title compound.

Workup

  1. stirringthe reaction was stirred at 0° C. for 4 hours
  2. extractionextracted with DCM (50 mL×3)
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel column

Sources & evidence

ORD record
ord-fccd30131d1047c593a82a48822f2da1
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

Loading…