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CAS No. : | 35216-39-8 | MDL No. : | MFCD03764428 |
Formula : | C7H9NO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MBNPJRQKQLLRIS-UHFFFAOYSA-N |
M.W : | 171.22 | Pubchem ID : | 428029 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen;palladium 10% on activated carbon; In methanol; for 2.333h;Inert atmosphere; | 2.0 g (0.0098 mol) of 4 was dissolved in 100 mL of methanol, and an aqueous suspension of Pd/C (10 %) was added under Ar atmosphere. The reaction mixture was additionally purged under Ar for 20 min. At this time, the reaction mixture was hydrogenated until the reduction was compiete. The reaction was stirred for 2 h. The precipitate was carefully filtered and the residue was collected under reduced pressure. Compound 5 was crystallized from ether and dried on air. The crude yield was 89 % (1.5 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With potassium phosphate; copper(l) iodide; C16H18N2O2; In dimethyl sulfoxide; at 90℃; for 24h;Schlenk technique; Inert atmosphere; | General procedure: Sodium alkylsulfinate or sodium arylsulfinate (6.5 mmol), copper iodide (of which the dosage was shown in the following table), ligand (of which the dosage was shown in the following table) and potassium phosphate (5.0 mmol) were added into a 10 mL Schlenk tube. The tube was evacuated and filled with argon for three times, and then aryl chloride (5 mmol) and 4 mL of DMSO were added. The reaction mixture was homogeneously stirred at corresponding temperature for 24 hours. After cooling, the contents of the of Schlenk tube were washed with ethyl acetate, and filtered through silica gel and diatomite plug. The filtrate was concentrated and purified by column chromatography to give the corresponding product. |
Step 2 Preparation of (3-amino)phenyl methyl sulphone (3-Nitro)phenyl methyl sulphone (prepared as described in Step 1 above) (5.396 g) reduced iron (7.5 g) and ammonium chloride (7.18 g) were mixed together in ethanol/water (2:1) (150 ml) and heated under reflux for 2 hours. The black solution was filtered through `Celite` and the pad washed with ethyl acetate. The solvents were removed under reduced pressure and the residue taken up in ethyl acetate/water. The organic layer was separated and the aqueous layer extracted with 3 further portions of ethyl acetate. The combined organic layers were washed with brine and the solvent removed under reduced pressure to give a dark orange oil (3.9275 g). This was chromatographed on silica gel using ethyl acetate-hexane (45:55 to 50:50) as eluant to give the title compound as an orange oil, yield 3.607 g. 1 H nmr (CDCl3): delta3.02 (3H, s), 3.8-4.2 (2H, broad s), 6.90 (1H, m), 7.18-7.38 (3H, m) | ||
With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; for 16h; | General procedure: A solution of 1 -ethyl-4-(4-nitro-2-(trifluoromethyl)benzyl)piperazine (step 2 intermediate)(800 mg, 2.52 mmol) in methanol (20 mL) with catalytic amount of 10% palladium oncarbon (50% wet) was hydrogenated at RT for 16 h. The mixture was filtered through celite and the celite bed was rinsed with methanol. The combined filtrate and washings were concentrated and the residue thus obtained was purified by silica gel column chromatography to yield 600 mg of the desired product. ?H NMR (400 MHz, DMSO-d6) oe 0.97 (t, J = 7.2 Hz,3H), 2.26-2.51 (m, 1OH), 3.38 (s, 2H), 5.44 (s, 2H), 6.74 (dd, J, = 2.4 Hz, J2 = 8.4 Hz, 1H),6.85 (s, 1H), 7.29 (t, J 8.4 Hz, 1H). |
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