4-Iodoaniline → HCID 62231418, compound

Temperature

80 °C

A mixture containing 4-iodoaniline (400 g, 1.83 mol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (263 g, 1.83 mol) was stirred at 80° C. After 2 hours, the mixture was cooled to 23° C. and then ethyl acetate (5 L) was added. The mixture was extracted with aqueous sodium hydroxide solution (110 g of sodium hydroxide dissolved in 5 L of water). The basic aqueous layer was washed with ethyl acetate (3 L). The washed layer was brought to pH 2 with 6 M aqueous hydrochloric acid solution. The acidic aqueous solution was extracted with ethyl acetate (3×3 L). The organic layers were combined and the combined solution was dried with magnesium sulfate. The dried solution was filtered and the filtrate was concentrated to afford the title compound as a yellow solid.

1. temperaturethe mixture was cooled to 23° C.
2. extractionThe mixture was extracted with aqueous sodium hydroxide solution (110 g of sodium hydroxide dissolved in 5 L of water)
3. washThe basic aqueous layer was washed with ethyl acetate (3 L)
4. extractionThe acidic aqueous solution was extracted with ethyl acetate (3×3 L)
5. dry with materialthe combined solution was dried with magnesium sulfate
6. filtrationThe dried solution was filtered
7. concentrationthe filtrate was concentrated

ORD record

ord-378f8363045e4f899e1aaf5e83b0c753

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09284308B2