Sulfate Ion → HCID 86759321, compound

HRID 1840669Notes

Reaction equation

[C:1](=[O:4])([O-])[O-].[K+].[K+].[C:7]([O:11][CH3:12])([CH3:10])([CH3:9])[CH3:8].CC(=O)[C:15](=[N:19]O)C(=O)C.S([O-])([O-])(=O)=O>O.CN(C)C=O>[CH3:7][N:19]([CH:1]=[O:4])[CH3:15].[CH3:8][C:7]([O:11][CH3:12])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: -5 °C

Procedure

4.5 kg (32.6 mol) of potassium carbonate were suspended in 3.2 1 of methyl tert-butyl ether and one liter of DMF in a 20 l vessel. The mixture was cooled to 0 to −10° C. with stirring. A solution of 4128 g (32 mol) of pentane-2,3,4-trione 3-oxime, 2 l of DMF and 4032 g (32 mol) of diemethyl [sic] sulfate was then metered in over the course of 2 hours at an internal temperature of <25° C. The mixture was then stirred at room temperature for 3.5 hours. 20 l of water was subsequently metered in, the upper organic phase was separated off, the aqueous phase was washed with 2 l of methyl tert-butyl ether, the combined organic phase were washed with 1 l of 5% strength hydrochloric acid, and the solvent was distilled off. 4214 g of the title compound were obtained in a purity of 96.6% (GC percent area) which corresponds to a yield of 89%.

Workup

customwas then metered in over the course of 2 hours at an internal temperature of <25° C
stirringThe mixture was then stirred at room temperature for 3.5 hours
customwas separated off
washthe aqueous phase was washed with 2 l of methyl tert-butyl ether
washthe combined organic phase were washed with 1 l of 5% strength hydrochloric acid
distillationthe solvent was distilled off

Sources & evidence

ORD record: ord-5b952fdf140e4c2881a03efb3657ab48
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680410B2

Reaction notes

Loading…