Acetonitrile → 187283-19-8

Temperature

40 °C

A mixture of 10.0 g (38.1 mMol) of 4-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]benzenepropanamide, 18.5 g (43 mMol) of I,I-bis-(trifluoroacetoxy)iodobenzene, 100 ml of acetonitrile and 20 ml of water was stirred for 8 hours at a reaction temperature of 40° C. A further 2.5 g of I,I-bis-(trifluoroacetoxy)iodobenzene were added and the mixture was again kept at 40° C. for 6 hours. The acetonitrile was distilled off in vacuo, the residue was taken up in 200 ml of water, then filtered, the filtrate was extracted once with 50 ml of diethylether and then made alkaline with sodium hydroxide. The alkaline aqueous phase was extracted three times with 100 ml of dichloromethane, the combined dichloromethane extracts were dried over sodium sulphate and freed from solvent in vacuo. The residue was purified by column chromatograph on silica gel (Macherey-Nagel, 35-70 mesh ASTM) using first of all tert.butyl-methylether and then tert.butylmethylether/methanol/conc. aqueous ammonia=9/1/0.3 (v/v/v) as eluant. 4.5 g (50% of theory) of a colourless oil were obtained.

1. waitthe mixture was again kept at 40° C. for 6 hours
2. distillationThe acetonitrile was distilled off in vacuo
3. filtrationfiltered
4. extractionthe filtrate was extracted once with 50 ml of diethylether
5. extractionThe alkaline aqueous phase was extracted three times with 100 ml of dichloromethane
6. dry with materialthe combined dichloromethane extracts were dried over sodium sulphate
7. customThe residue was purified by column chromatograph on silica gel (Macherey-Nagel, 35-70 mesh ASTM)
8. custom4.5 g (50% of theory) of a colourless oil were obtained

ORD record

ord-c16d15b4c06f4c4b8c3756507d5c20e6

Source dataset

uspto-grants-2000_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06114390