Dimethyl Sulfide → HCID 90411474, compound

HRID 1503160Notes

Reaction equation

HRID 1503160 reaction equation
[Cl:1]N1C(=O)CCC1=O.CSC.[F:12][C:13]([F:35])([F:34])[O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21]/[N:22]=[CH:23]/[C:24]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=2)=[CH:17][CH:16]=1>C(Cl)Cl>[Cl:1][C:23](=[N:22][NH:21][C:18]1[CH:19]=[CH:20][C:15]([O:14][C:13]([F:34])([F:35])[F:12])=[CH:16][CH:17]=1)[C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 31398ChlorosuccinimideHCID 90411589HCID 90411589, compound

Product 1

HCID 90411474HCID 90411474, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a magnetically stirred solution of N-chlorosuccinimide (0.59 g, 4.43 mmoL) in CH2Cl2 (8 mL) at 0° C. was added dimethyl sulfide (0.85 mL, 8.87 mmoL) and the reaction mixture was stirred for 15 minutes (min) and then cooled to −78° C. To this solution was added (E)-methyl 4-((2-(4-(trifluoromethoxy)-phenyl)hydrazono) methyl)benzoate dissolved in 8 mL of CH2Cl2 and the reaction mixture was stirred at this temperature for 1 hour (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 silica gel (SiO2) loading cartridge and purified via flash column chromatography (Gradient EtOAc/hexanes). The title compound was obtained as a yellow solid as a mixture of E and Z isomers: mp 159-162° C.; 1H NMR (400 MHz, CDCl3) δ 8.18 (s, 1H), 8.07 (d, J=8.8 Hz, 2H), 7.98 (d, J=8.8 Hz, 2H), 7.20 (s, 4H), 3.95 (s, 3H); 19F NMR (376 MHz, CDCl3) δ−58.32; ESIMS m/z 372 ([M+H])+.

Workup

  1. stirringthe reaction mixture was stirred at this temperature for 1 hour (h)
  2. temperaturewarmed to room temperature
  3. stirringstirred for 2 h
  4. concentrationThe solution was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in CH2Cl2 (15 mL)
  6. additionadded to a silica gel (SiO2) loading cartridge
  7. custompurified via flash column chromatography (Gradient EtOAc/hexanes)

Sources & evidence

ORD record
ord-5a14351b8543475388410be8927cc6c1
Source dataset
uspto-grants-2015_12
Patent number
US09212150B2

Reaction notes

Loading…