Diisopropylamine → N-Methoxy-N-methyl-1-(propan-2-yl)-1H-benzotriazole-6-carboxamide
Reaction equation
[CH:1]([N:4]1[C:8]2[CH:9]=[C:10]([C:13]([OH:15])=O)[CH:11]=[CH:12][C:7]=2[N:6]=[N:5]1)([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.C(NC(C)C)(C)C.Cl.[CH3:30][NH:31][O:32][CH3:33]>C(Cl)Cl.CN(C=O)C>[CH3:33][O:32][N:31]([CH3:30])[C:13]([C:10]1[CH:11]=[CH:12][C:7]2[N:6]=[N:5][N:4]([CH:1]([CH3:2])[CH3:3])[C:8]=2[CH:9]=1)=[O:15]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a stirred mixture of 3-isopropyl-3H-benzotriazole-5-carboxylic acid (9 g) in 150 mL of methylene chloride and 0.15 mL of DMF was added 5.0 mL of oxalyl chloride. The solution was stirred overnight before 27 mL of N,N-diisopropylamine and 5.6 g of N,O-dimethylhydroxylamine hydrochloride was added. The mixture was stirred for 3 days before mixture was washed with a solution of sodium dihydrogenphosphate, aqueous bicarbonate, dilute hydrochloric acid, brine, dried (sodium sulfate), filtered, and the filtrate was concentrated to a dark oil. This oil was purified by flash chromatography (eluting with 3:2 ethyl acetate/hexanes) to afford 10.4 g of 3-isopropyl-3H-benzotriazole-5-carboxylic acid methoxy-methyl-amide as brown oil.
Workup
- additionwas added
- washwas washed with a solution of sodium dihydrogenphosphate, aqueous bicarbonate, dilute hydrochloric acid, brine
- dry with materialdried (sodium sulfate)
- filtrationfiltered
- concentrationthe filtrate was concentrated to a dark oil
- customThis oil was purified by flash chromatography (eluting with 3:2 ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-6f63fffdd93847e2b086fca0ea0dbea8
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06664395B2
Reaction notes
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