Dimethyl Sulfate → HCID 13328924, compound

HRID 232000Notes

Reaction equation

HRID 232000 reaction equation
[N:1]([C:4]([F:16])([F:15])[C:5]([F:14])([O:9][C:10]([F:13])([F:12])[F:11])[C:6]([O-:8])=[O:7])=[N+:2]=[N-:3].[Na+].S(OC)(O[CH3:22])(=O)=O>>[N:1]([C:4]([F:15])([F:16])[C:5]([F:14])([O:9][C:10]([F:12])([F:13])[F:11])[C:6]([O:8][CH3:22])=[O:7])=[N+:2]=[N-:3]

Participants

3

Reactant 2

HCID 6497Dimethyl SulfateHCID 13328922HCID 13328922, compound

Product 1

HCID 13328924HCID 13328924, compoundYield 84%

Procedure

The resulting solution, which contained sodium 3-azido-2-trifluoromethoxytrifluoropropionate, was stirred with 69.3 g (0.55 mole) of dimethyl sulfate for 3 hr. until an initial exothermic reaction subsided. Volatiles were removed at 50° (2 mm, 2.6×10-1 kPa), and the resulting crude ester was fractionated to yield 111.8 g (84%) of methyl 3-azido-2-trifluoromethoxytrifluoropropionate, bp 38°-41° (24 mm, 2.1 kPa). IR (CCl4): 3010, 2960, and 2850 (sat'd CH); 2150 (N3), 1780 (C=O), and 1100-1250 cm-1 (C-F). NMR (CCl4): 1H 3.89 ppm (s, OCH3); 19F-56.0 (d, JFF 8.6 Hz, 3F, OCF3) and -131.6 ppm (q of t, JFF 8.6, 5 Hz, 1F, CF) with an AB for CF2N3 at -8333 and -8521 Hz (d, JFF 5.0 Hz, 1F) and -8548 and -8763 Hz (d, JFF 5.6 Hz, 1F).

Workup

  1. customuntil an initial exothermic reaction
  2. customVolatiles were removed at 50° (2 mm, 2.6×10-1 kPa)

Sources & evidence

ORD record
ord-41fe1c9c796a4d63af353ec37046b624
Source dataset
uspto-grants-1989_07
Patent number
US04851161

Reaction notes

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