Ammonia → 2,2,3,3-Tetrafluoro-3-methoxypropanamide

HRID 1680422Notes

Reaction equation

HRID 1680422 reaction equation
[CH3:1][O:2][C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5](OC)=[O:6].[NH3:13]>CCOCC>[CH3:1][O:2][C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([NH2:13])=[O:6]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 69787Propanoic acid, 2,2,3,3-tetrafluoro-3-methoxy-, methyl ester

Product 1

HCID 205200792,2,3,3-Tetrafluoro-3-methoxypropanamideYield 95.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 140 g (0.74 mol) of methyl 3-methoxytetrafluoropropionate in 100 ml of ether was treated at 0° with 15.3 g (0.90 mol) of NH3. The resulting viscous mixture was stirred at 25° overnight and evaporated to dryness at 25° (10 mm). The crude residue was then recrystallized from ether/hexane to give 123.6 g (95%) of 3-methoxytetrafluoropropionamide, mp 78°-80°. An analytical sample was recrystallized from ether/hexane, mp 83°-85°. IR (KBr): 2.95, 3.02 and 3.10 (NH2), 3.37 and 3.49 (sat'd CH), 5.92 (C=O), 6.19 (NH2), 7.5-10μ (CF, C--O). NMR ((CD3)2CO): 1H 6.67 (broad, 2H, NH2) and 3.66 ppm (s, 3H, OCH3); 19F-120.6 (t, JFF 4.7 Hz, 2F, CF2) and -121.8 ppm (t, JFF 4.7 Hz, of d, JHF 2.1 Hz, 2F, CF2).

Workup

  1. customevaporated to dryness at 25° (10 mm)
  2. customThe crude residue was then recrystallized from ether/hexane

Sources & evidence

ORD record
ord-02303a172ff14a088badd841bf5d0519
Source dataset
uspto-grants-1981_06
Patent number
US04273729

Reaction notes

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