Hydrochloric Acid → HCID 42629164, compound
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([S:9](Cl)(=O)=O)=[CH:4][C:3]=1[N+:13]([O-])=O.Cl>[Zn].C(O)C>[F:1][C:2]1[C:3]([NH2:13])=[CH:4][C:5]([SH:9])=[C:6]([CH3:8])[CH:7]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
156.9 g (2.4 mol) of zinc, 500 ml of ethanol and then 77 g (0.3 mol) of 4-fluoro-6-methyl-3-nitrobenzenesulfonyl chloride were placed in a 2-liter eggplant-shaped flask equipped with a mechanical stirrer, a thermometer and a dropping funnel. Thereinto was dropped 500 g (5 mol) of hydrochloric acid in a water bath so that the temperature of the reaction system did not exceed 50° C., followed by stirring at 75° C. for 6 hours. Ethanol was distilled off under reduced pressure; the residue was cooled to room temperature; sodium bicarbonate was added to neutralize the reaction system; extraction was conducted twice with ethyl acetate; the ethyl acetate layer was washed with water and then with a saturated aqueous sodium chloride solution. The ethyl acetate layer was dried with anhydrous sodium sulfate and subjected to distillation under reduced pressure to distil off ethyl acetate to obtain 41 g of a title compound at a yield of 87%.
Workup
- customequipped with a mechanical stirrer
- customdid not exceed 50° C.
- distillationEthanol was distilled off under reduced pressure
- temperaturethe residue was cooled to room temperature
- additionsodium bicarbonate was added
- extractionextraction
- washthe ethyl acetate layer was washed with water
- dry with materialThe ethyl acetate layer was dried with anhydrous sodium sulfate
- distillationsubjected to distillation under reduced pressure
- customto distil off ethyl acetate
Sources & evidence
- ORD record
- ord-eae6ada18a4a46f7a3e05c2791ca5f85
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08334410B2
Reaction notes
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