Acetic Acid → HCID 12348626, compound

Temperature

100 °C

10 g (65.7 mmol) of phenylthiourea 37 were dissolved in 100 ml of acetic acid. 9.9 ml of the acetal 38 were added and the mixture was heated at 100° C. for 2 h. The solvent was removed i.v. and the residue was partitioned between 300 ml of 1N NaOH and 300 ml of ethyl acetate. The aqueous phase was extracted twice with in each case 100 ml of ethyl acetate and the combined organic phases were dried using magnesium sulfate. The solvent was removed and the residue was precipitated from 50 ml of diisopropyl ether. The solid was filtered off with suction and dried at 50° C. i.v. 2.5 g of aniline 39 were obtained. The diisopropyl ether mother liquor was evaporated and the residue was chromatographed on silica gel using heptane/ethyl acetate 2:1. This resulted in a further 3.5 g of 39 being obtained. Yield 6.0 g (52%).

1. customThe solvent was removed i.v
2. customand the residue was partitioned between 300 ml of 1N NaOH and 300 ml of ethyl acetate
3. extractionThe aqueous phase was extracted twice with in each case 100 ml of ethyl acetate
4. customthe combined organic phases were dried
5. customThe solvent was removed
6. customthe residue was precipitated from 50 ml of diisopropyl ether
7. filtrationThe solid was filtered off with suction
8. customdried at 50° C. i.v

ORD record

ord-c268aadefd904b75be13a6b780cb8d5d

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08778955B2