Trimethylamine → HCID 13581307, compound

HRID 232007Notes

Reaction equation

HRID 232007 reaction equation
[CH3:1][N:2]([CH3:4])[CH3:3].[CH3:5][S:6]([C:9]([F:18])([F:17])[C:10]([F:16])([F:15])[C:11]([O:13]C)=[O:12])(=[O:8])=[O:7]>CCOCC>[CH3:5][S:6]([C:9]([F:17])([F:18])[C:10]([F:15])([F:16])[C:11]([O-:13])=[O:12])(=[O:8])=[O:7].[CH3:1][N+:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 13581302Methyl 2,2,3,3-tetrafluoro-3-(methanesulfonyl)propanoate

Product 1

HCID 13581307HCID 13581307, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Trimethylamine (12.4 g, 0.21 mol) was distilled into a stirred solution of 47.8 g (0.20 mol) of methyl 3-methylsulfonyltetrafluoropropionate in 100 ml of ether. The mixture was stirred overnight, filtered under nitrogen, and the solid dried under vacuum. There was thus obtained 52.1 g (88%) of tetramethylammonium 3-methylsulfonyltetrafluoropropionate, mp 98° to 100°, as deliquescent crystals. NMR (DMSO-d6): 1H 3.40 (t, JHF 2 Hz, 3H, CH3SO2) and 3.17 ppm (s, 12H, (CH3)4N+); 19F-112.3 (t, JFF 3.0 Hz, 2F, CF2C=O) and -114.4 ppm (T, JFF 3.0 Hz, of m, 2F, CF2SO2). Anal. Calcd. for C8H15F4NO4S: C, 32.32; H, 5.09; N, 4.7. Found: C, 32.20; H, 5.17; N, 4.44.

Workup

  1. filtrationfiltered under nitrogen
  2. customthe solid dried under vacuum

Sources & evidence

ORD record
ord-be687f5ce4fb4ea3be4df73effdcb1f4
Source dataset
uspto-grants-1989_07
Patent number
US04851161

Reaction notes

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