Ammonium Hydroxide → 2-Iodotetrafluoropropionamide

Temperatur

12.5 °C

Into a glass flask was placed a mixture of aqueous ammonium hydroxide (28 wt. %, 40.5 mL, 0.6 mol) and methylene chloride (80 mL) which was cooled to 10-15° C. 2-Iodohexafluoropropyl fluorosulfate from Experiment 5 (37.6 g, 0.1 mol) was added slowly with vigorous stirring while the reaction temperature was kept at <15° C. After addition, the mixture was warmed to ambient temperature, the bottom organic layer was separated, washed with aqueous sodium bisulfite solution, dried over MgSO4. The solvent was removed in vacuo to give the title product as a white solid (18.5 g, 68.3 % yield), mp. 75-77° C., 1H NMR (300 MHz, CDCl3): δ6.98, 6.53 (2 broad singlets); 19F NMR (188.24 MHz, CDCl3): -76.3 (2 singlets, 3F), -138.5 (m, 1F); IR: 1690 cm-1 (C=O); Anal. Calcd. for C3H2F4INO: C: 13.30, H: 0.74, F: 28.05, N: 5.17. Found: C: 13.68, H: 0.83, F: 28.43, N: 5.21. Mass. Calcd. for [M+ ]: 270.9117; Found: 270.9093.

1. customInto a glass flask was placed
2. customwas kept at <15° C
3. additionAfter addition
4. temperaturethe mixture was warmed to ambient temperature
5. customthe bottom organic layer was separated
6. washwashed with aqueous sodium bisulfite solution
7. dry with materialdried over MgSO4
8. customThe solvent was removed in vacuo

ORD-Eintrag

ord-2117c74a41ed4b4984d1d89d0207d8d1

Quelldatensatz

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06166157