Dimethyl Sulfide → 4-Nitro-N'-(4-(trifluoromethoxy)phenyl)-benzohydrazonoyl chloride
Reaction equation
[Cl:1]N1C(=O)CCC1=O.CSC.[N+:12]([C:15]1[CH:34]=[CH:33][C:18]([CH:19]=[N:20][NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)([O-:14])=[O:13]>C(Cl)Cl>[N+:12]([C:15]1[CH:16]=[CH:17][C:18]([C:19]([Cl:1])=[N:20][NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][C:29]([F:30])([F:31])[F:32])=[CH:24][CH:23]=2)=[CH:33][CH:34]=1)([O-:14])=[O:13]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a magnetically stirred solution of N-chlorosuccinimide (1.23 g, 9.22 mmoL) in CH2Cl2 (16 mL) at 0° C. was added dimethyl sulfide (1.36 mL, 18.45 mmoL) and the reaction mixture was stirred for 15 min and then cooled to −78° C. To this solution was added 1-(4-nitrobenzylidene)-2-(4-(trifluoromethoxy)-phenyl)hydrazine (2 g, 6.15 mmoL) dissolved in CH2Cl2 (16 mL) and the reaction mixture was stirred at this temperature for 1 h, warmed to room temperature and stirred for 2 h. The solution was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (15 mL) and added to a SiO2 loading cartridge and purified via flash column chromatography (Gradient EtOAc/hexanes). The title compound was isolated as a yellow solid: mp 172-175° C.; 1H NMR (400 MHz, CDCl3) δ 8.29-8.26 (m, 3H), 8.09-8.05 (m, 3H), 7.22 (s, 4H); 19F NMR (376 MHz, CDCl3) δ −58.30; ESIMS m/z 359 ([M+H])+.
Workup
- stirringthe reaction mixture was stirred at this temperature for 1 h
- temperaturewarmed to room temperature
- stirringstirred for 2 h
- concentrationThe solution was concentrated under reduced pressure
- dissolutionThe residue was dissolved in CH2Cl2 (15 mL)
- additionadded to a SiO2 loading cartridge
- custompurified via flash column chromatography (Gradient EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-3f2a294fe54d4323a169262fafbab55c
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09212150B2
Reaction notes
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