Dimethyl Sulfate → 4-(Dimethylamino)-2(5H)-furanone

HRID 1879317Notes

Reaction equation

[CH3:1][NH:2][C:3]1[CH2:7][O:6][C:5](=[O:8])[CH:4]=1.[OH-].[Na+].S(OC)(O[CH3:15])(=O)=O>COCCOC>[CH3:1][N:2]([CH3:15])[C:3]1[CH2:7][O:6][C:5](=[O:8])[CH:4]=1

Participants

Conditions

Temperature: 40 °C

Procedure

2 g (0.18 mol) of 4-(methylamino)furan-2(5H)-one are introduced in 20 ml of 1,2-dimethoxyethane, and 0.72 g of sodium hydroxide is added. 2.2 g of dimethyl sulphate in 5 ml of 1,2-dimethoxyethane are metered into the suspension and stirred at 40° C. for 5 h. The solvent is removed in vacuo and 50 ml of water are added to the residue. This mixture is then extracted with 50 ml of dichloromethane. The organic phase is dried over sodium sulphate and then evaporated down in vacuo. 1.2 g of 4-(dimethylamino)furan-2(5H)-one are obtained as a solid with a purity of 96% (yield 51%).

Workup

customThe solvent is removed in vacuo and 50 ml of water
additionare added to the residue
extractionThis mixture is then extracted with 50 ml of dichloromethane
dry with materialThe organic phase is dried over sodium sulphate
customevaporated down in vacuo

Sources & evidence

ORD record: ord-ed36f12a42914b47ace6d8109ec09211
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314242B2

Reaction notes

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