Triethylamine → N'-(6-Chloro-5-(trimethylsilyl)pyridazin-3-yl)-2-fluorobenzohydrazide
Reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:12][NH2:13])=[CH:6][C:7]=1[Si:8]([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C.[F:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>C(OCC)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:12][NH:13][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][CH:29]=[CH:30][C:22]=2[F:21])=[CH:6][C:7]=1[Si:8]([CH3:9])([CH3:10])[CH3:11]Participants
5
Procedure
A solution of 21 (6.45 g, 30 mmol) and triethylamine (5 mL, 36 mmol) in diethyl ether (120 mL) was cooled to 0-5° C. in an ice bath. 2-Fluorobenzoyl chloride (4.8 g, 30 mmol) was added dropwise keeping the temperature less than 5° C. The reaction was stirred 30 min then quenched by the addition of anhydrous MeOH (0.4 mL). The mixture was diluted with hexane (100 mL) and filtered. The solids were washed with ether (2×15 mL), then water (30 mL). The solids were dissolved in dichloromethane (100 mL) with a small amount of MeOH to aid solubility, then washed with brine. The organic solution was dried over Na2SO4 and concentrated to give a 51.7% yield of 22 as a brownish solid.
Workup
- customthe temperature less than 5° C
- customthen quenched by the addition of anhydrous MeOH (0.4 mL)
- additionThe mixture was diluted with hexane (100 mL)
- filtrationfiltered
- washThe solids were washed with ether (2×15 mL)
- dissolutionThe solids were dissolved in dichloromethane (100 mL) with a small amount of MeOH
- washwashed with brine
- dry with materialThe organic solution was dried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-d34fd1bb6e3b4b41853a117f9f75731a
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08501738B2
Reaction notes
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