Phenol → Methylsulfamic acid phenyl ester

Temperature

110 °C

The reaction flask was charged with 34.1 g (0.20 mole) of methylaminosulfonyl chloride, 18.8 g (0.20 mole) of phenol and 150 ml of toluene. The dark, red solution was heated at 110° C. for 16 hours. The solution was cooled and washed with a solution of 16 g of sodium bicarbonate in 80 ml water. The toluene solution was washed with water then stirred with Type 3A molecular sieve powder and Norite "A" activated charcoal. After filtration, the filtrate was concentrated to 32.7 g of oil (87% crude yield). The oil was dissolved in 100 ml methylene chloride and chromatographed on silica gel. The main fraction was concentrated to an oil which solidified after chilling for 3 days. The solid was triturated with petroleum ether to give 16.1 g of solid, mp 43°-45° C. A recrystallization from a mixture of isopropyl acetate (2 ml/g) and petroleum ether (4 ml/g) gave 12.3 g of solid, mp 44°-46° C.

1. temperatureThe solution was cooled
2. washwashed with a solution of 16 g of sodium bicarbonate in 80 ml water
3. washThe toluene solution was washed with water
4. filtrationAfter filtration
5. concentrationthe filtrate was concentrated to 32.7 g of oil (87% crude yield)
6. dissolutionThe oil was dissolved in 100 ml methylene chloride
7. customchromatographed on silica gel
8. concentrationThe main fraction was concentrated to an oil which
9. temperatureafter chilling for 3 days
10. customThe solid was triturated with petroleum ether

ORD record

ord-a2e7d1cb407340ce8cab9d475cd8e819

Source dataset

uspto-grants-1993_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05273993