Triethylamine → HCID 13581309, compound

HRID 232004Notes

Reaction equation

HRID 232004 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]([F:12])([F:11])[C:5]([F:10])([F:9])[N:6]=[N+:7]=[N-:8].[CH2:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[CH3:15]>CCOCC>[CH3:1][N+:16]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:14][CH3:15].[N:6]([C:5]([F:9])([F:10])[C:4]([F:12])([F:11])[C:3]([O-:13])=[O:2])=[N+:7]=[N-:8]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 10921558HCID 10921558, compound

Product 1

HCID 13581309HCID 13581309, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 37.0 g (0.184 mole) of methyl-3-azidotetrafluoropropionate, prepared as in Example 9, 20.2 g (0.20 mole of triethylamine, and 50 ml of ether was stirred at 25°. A second layer slowly formed. The reaction was stopped after 24 days, at which time the second layer was not increasing in volume. Evaporation of volatiles under full pump vacuum left 54.9 g (99% of theory) of methyltriethylammonium 3-azidotetrafluoropropionate as a moist solid. IR(CHCl3): 3020 (sat'd CH), 2170 (N3), 1690 (CO2), and 1250-1100 cm-1 (CF). NMR (DMSO-d6): 1H 3.31 (q, JHH 7 Hz, 6H, CH2), 2.93 (s, 3H, NCH3), and 1.22 ppm (t, JHH 7 Hz, 9H, CH3); 19F -90.8 (t, JFF 6.3 Hz, 2F, CF2N3) and -115.6 ppm (t, JFF 6.3 Hz, 2F, CF2C=O).

Workup

  1. customA second layer slowly formed
  2. temperaturethe second layer was not increasing in volume
  3. customEvaporation of volatiles under full pump vacuum
  4. waitleft 54.9 g (99% of theory) of methyltriethylammonium 3-azidotetrafluoropropionate as a moist solid

Sources & evidence

ORD record
ord-3d86b7aa2917491283422fe9f9f954b5
Source dataset
uspto-grants-1989_07
Patent number
US04851161

Reaction notes

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