Triethylamine → Benzotriazol-1-yl(cyclopropyl)methanone

HRID 2251562Notes

Reaction equation

HRID 2251562 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.C(N(CC)CC)C.[CH:17]1([C:20](Cl)=[O:21])[CH2:19][CH2:18]1>C(Cl)Cl>[CH:17]1([C:20]([N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[N:2]2)=[O:21])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 178418385HCID 178418385, compound

Product 1

HCID 903307Benzotriazol-1-yl(cyclopropyl)methanoneYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0C solution of benzotriazole (5.05 g, 42.39 mmol) in CH2Cl2 (100 mL) was added dropwise triethylamine (9.0 ml, 64.57 mmol) followed by cyclopropyl carbonyl chloride (4.2 ml, 46.28 mmol). The mixture was stirred at rt for 1 h and then quenched with a solution of 2N aqueous HCl (75 ml). The organic phase was washed with 2 N HCl (2×75 mL) and water (100 ml), dried with MgSO4 and concentrated in vacuo. The solid residue was washed with hexenes, filtered and dried to yield 1-(cyclopropylcarbonyl)-1H-1,2,3-benzotriazole as a white solid (5.92 g, 75%).

Workup

  1. customquenched with a solution of 2N aqueous HCl (75 ml)
  2. washThe organic phase was washed with 2 N HCl (2×75 mL) and water (100 ml)
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo
  5. washThe solid residue was washed with hexenes
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-7d3313e2f8504d73802fd51dbff3d016
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

Loading…