4-Toluenesulfonyl chloride → HCID 3296813, compound

A mixture of sodium azide (683 mg, 10.5 mmol), p-toluenesulfonyl chloride (2.0 grams, 10.5 mmol), and 70% aqueous ethanol (30 mL) was stirred at room temperature for 1 hour. Diethyl malonate (1.62 mL, 10.0 mmol) and triethylamine (1.46 mL, 10.5 mmol) were added. The reaction mixture was stirred at room temperature for 1.5 hours and then poured into deionized water (200 mL). The mixture was extracted with petroleum ether. The extracts were combined and decanted from the solid that formed. The petroleum ether solution was washed with a saturated aqueous sodium chloride solution. The organic solution was dried using anhydrous magnesium sulfate, filtered, and concentrated to give 1.65 grams of diethyl 2-diazomalonate as a yellow oil. IR (KBr): 2138, 1757, 1735, 1320, 1092 cm-1. Decomposition temperature: 175° C. (by DSC).

1. stirringThe reaction mixture was stirred at room temperature for 1.5 hours
2. extractionThe mixture was extracted with petroleum ether
3. customdecanted from the solid
4. customthat formed
5. washThe petroleum ether solution was washed with a saturated aqueous sodium chloride solution
6. customThe organic solution was dried
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-259ec1b3244a488292360c6ca67d68ba

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05691098