Sodium Sulfite → (4-Nitrophenyl)methanesulfonyl chloride

温度

90 °C

A mixture of 4-nitrobenzyl bromide (100.0 g 0.46 mol), sodium sulphite (84.8g, 0.67 mol) and water (316 ml) was heated at 90° C. for 5 h. The solution was cooled and the resultant solid filtered and washed with diethyl ether. The product was dried under vacuum at 60° C. (95 g, 86%). Phosphorus pentachloride (78 g, 0.375 mol ) was added to sodium 4-nitrobenzyl sulphonate (60 g, 0.25 mol) and the mixture heated at 90° C. for 2 h. The mixture was cooled and volatile material removed under vacuum. The residue was dissolved in dichloromethane (500 ml) and water (150 ml). The organic layer was separated, dried over anhydrous sodium sulphate, filtered and evaporated to give 4-nitrobenzyl sulphonyl chloride (48.9 g, 83%) which was pure by 1H NMR. Methylamine gas was bubbled through a solution of 4-nitrobenzyl sulphonyl chloride (37.9 g, 0.16 mol), in dichloromethane (325 ml), until uptake had ceased (0.5 h). The resulting solid was filtered, washed with H2 and dried under vacuum to give the title-sulphonamide (32.5 g, 88%), δ(250MHz, D6 -DMSO) 2.61 (3H, s, Me), 4.55 (2H, s, CH2), 7.06 (1H, s, NH), 7.66 (2H, d, J=8.7Hz, Ar-H), 8.25 (2H, d, J=8.7Hz, Ar-H).

1. temperatureThe solution was cooled
2. filtrationthe resultant solid filtered
3. washwashed with diethyl ether
4. customThe product was dried under vacuum at 60° C. (95 g, 86%)
5. temperaturethe mixture heated at 90° C. for 2 h
6. temperatureThe mixture was cooled
7. customvolatile material removed under vacuum
8. dissolutionThe residue was dissolved in dichloromethane (500 ml)
9. customThe organic layer was separated
10. dry with materialdried over anhydrous sodium sulphate
11. filtrationfiltered
12. customevaporated

ORDレコード

ord-72d9c837372848a2bee4c84598a2fec6

出典データセット

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05854247