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CAS No. : | 7006-52-2 | MDL No. : | MFCD00052014 |
Formula : | C7H8ClN | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | WFGYSQDPURFIFL-UHFFFAOYSA-N |
M.W : | 141.60 | Pubchem ID : | 138900 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
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 |
---|---|---|
67% | With pyridine; at 20℃; for 3h; | To a solution of N-methyl-3-chloroaniline (643 muL, 5.25 mmol ) in anhydrous pyridine (3,8 h) was added methyl 2- (chlorosulfonyl) benzoate (1.17 g, 5.00 mmol), and the resulting was then diluted with CH2CI2 (35 rrtL) , washed with 7% aqueous HC1 (2 x 35 mL) , brine (35 mL) , saturated aqueous NaHCCh (35 mL) , and brine again (35 mL) , dried over Na:S04, and concentrated to provide pure sulfonamide 2x as a viscous yellow oil (1.14 g, 67%) . To a solution of sulfonamide 2x (1.09 g, 3.21 mmol) in MeOH (8.2 mL) was added water (4.1 mL) and NaOH (385 mg, 3.21 mmol), and the resulting mixture was refluxed for 45 minutes. The solution was diluted with water (50 mL) , washed with Et20 (30 mL) , made strongly acidic with 10% aqueous HC1, and extracted with CH2CI2 (30 mL, 2 x 20 mL) . The combined organics were washed with water (20 mL) , dried over Na S04, and concentrated to provide the pure carboxylic acid intermediate as a yellow solid (1.04 g, 99%). The carboxylic acid (1.00 g, 3.07 mmol) was dissolved in thionyl chloride (6.6 mL) , and the resulting solution was stirred for 2 h and then concentrated in vacuo to provide the intermediate acyl chloride as a tan solid. This material was dissolved in CHCI3 (13 itiL) , aluminum chloride (1.31 g, 9.82 mmol) was added, and the resulting mixture was refluxed for 1 h. The reaction was then quenched with ice water (100 mL) and extracted with CH2C12 (50 mL, 2 x 25 mL) . The combined organics were washed with water (50 mL) , dried over aaSO^ and concentrated to give the crude product as a viscous brown oil. When a small quantity of MeOH was added to this oil , tan crystals formed. These we e crushed up and the supernatant was removed by pipet . The crystals w re washed with an additional small portion of ice-cold MeOH and then recrystallized from MeOH to provide pure ketone 3x as glistening tan needles (400 mg, 42%). NMR (500 MHz , CDC13) delta 8.27 (d, J = 8.6 Hz, 1H) , 7.97 - 7.91 (m, 2H) , 7.76 - 7.70 (m, 2H) , 7.35 - 7.30 (m, 2H) , 3.35 (s, 3H) ; 13C NMR (126 MHz , CDC13) delta 189.9, 142.8, 140.8, 136.8, 136.3, 133.6, 133.5, 132.3, 131.7, 129.2, 126.2, 125.3, 124.1, 38.8; LR-MS calcd. for C-^HuClNO^S [M+H] ' 308.01, found 308.47. |
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