Phosgene → Benzotriazole-1-carbonyl chloride
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:10](Cl)([Cl:12])=[O:11]>O1CCCC1.C1(C)C=CC=CC=1>[N:1]1([C:10]([Cl:12])=[O:11])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 22.5 °C
Procedure
A solution of 1H-benzo[d][1,2,3]triazole (0.5 g, 4.20 mmol) in tetrahydrofuran (25 ml) was added dropwise to a stirred 20% solution of phosgene (5.30 ml, 10.1 mmol) in toluene at 0-5° C. The reaction mixture was allowed to stir at 20-25° C. for 2 h (reaction complete by TLC). Argon was bubbled through the solution for 15 min. Then the solvent was evaporated in vacuum to give 1H-benzo[d][1,2,3]triazole-1-carbonyl chloride (0.763 g, 4.20 mmol) as a clear oil. The product was used without further purification. Pyridine (0.357 ml, 4.41 mmol) was added dropwise to a stirred solution of the oil in Tetrahydrofuran (25 ml) at 0-5° C. This was followed by a dropwise addition of N-methylcyclohexanamine (0.499 g, 4.41 mmol) at 0-5° C. The reaction mixture was allowed to stir overnight at 20-25° C. Water and EtOAc were added and the organic layer was separated, washed with 1M HCl, water and brine. The organic layer was dried (MgSO4) and evaporated in vacuum to give a clear oil. The oil was recrystallised from 2-propanol/DCM, the solid was collected, dried in vacuum at 40-45° C. Yield 230 mg (21%).
Workup
- custom(reaction complete by TLC)
- customArgon was bubbled through the solution for 15 min
- customThen the solvent was evaporated in vacuum
Sources & evidence
- ORD record
- ord-68ace5594bfa4fa69127cb7a6cc0cde4
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09353082B2
Reaction notes
Loading…