Trimethylamine → HCID 13581305, compound

HRID 1632156Notes

Reaction equation

HRID 1632156 reaction equation
[CH3:1][N:2]([CH3:4])[CH3:3].[N:5]([C:8]([F:17])([F:16])[C:9]([F:15])([F:14])[C:10]([O:12]C)=[O:11])=[N+:6]=[N-:7]>CCOCC>[CH3:1][N+:2]([CH3:8])([CH3:4])[CH3:3].[N:5]([C:8]([F:16])([F:17])[C:9]([F:15])([F:14])[C:10]([O-:12])=[O:11])=[N+:6]=[N-:7]

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 10921558HCID 10921558, compound

Product 1

HCID 13581305HCID 13581305, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Trimethylamine (10.6 g, 0.18 mole) was distilled into a solution of 37.0 g (0.184 mole) of methyl 3-azidotetrafluoropropionate, prepared as in Example 9, in 100 ml of ether. Precipitation of product was accompanied by a small exotherm. The reaction was determined by gas chromatography to be nearly complete after 4 hr. The mixture was stirred overnight, then evaporated under vacuum until dry. The residue was 31.8 g (68%) of tetramethylammonium-3-azidotetrafluoropropionate, mp 144°-145° (dec.). IR (nujol): 2170 (N3), 1680 (broad, CO21-), and 1250-1100 cm-1 (CF), NMR (DMSO-d6): H 3,25 ppm (s, CH3); 19F -90.8 (t, JFF 6.2 Hz, 2F, CF2N3) and -115.8 ppm (t, JFF 6.2 Hz, 2F, CF2C=O).

Workup

  1. customPrecipitation of product
  2. customevaporated under vacuum
  3. customuntil dry

Sources & evidence

ORD record
ord-44cfa2b4acba47079b65ddd85bc63552
Source dataset
uspto-grants-1984_10
Patent number
US04474700

Reaction notes

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