Carbonyl fluoride → HCID 20225813, compound

HRID 1248979Notes

Reaction equation

HRID 1248979 reaction equation
[CH2:1]([N:3]([Si](C)(C)C)[CH2:4][CH3:5])[CH3:2].[CH2:10]([N:12]([S:15](F)(F)[F:16])[CH2:13][CH3:14])[CH3:11].[C:19]([F:22])([F:21])=[O:20]>C(#N)C>[F:21][C:19]([F:16])([F:22])[O-:20].[CH2:1]([N:3]([S+:15]([N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[N:12]([CH2:13][CH3:14])[CH2:10][CH3:11])[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 3

HCID 9623Carbonyl fluorideHCID 70454(Diethylamino)trimethylsilaneHCID 123472(Diethylamino)sulfur trifluoride

Product 1

HCID 20225813HCID 20225813, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diethylaminotrimethylsilane (29.06 g, 0.2 mol) was added dropwise to a solution of 12.5 mL (0.1 mol) of diethylaminosulfur trifluoride in 75 mL of acetonitrile at 25°. The reaction mixture was stirred overnight, and then saturated with carbonyl fluoride. Evaporation of the solvent under reduced pressure gave 30.3 g (91%) of the trifluoromethoxide: mp 85°-95°; 1H NMR (CD3CN) δ1.21 ppm (t, J=7H, 9H), 3.29 ppm (q, J=7 Hz, 6H); F NMR (CD3CN) δ-20.8 ppm. Anal. Calcd. for C13H30F3N3OS: C, 46.83; H, 9.07; F, 17.07; N, 12.60. Found: C, 46.53; H, 9.17; F, 17.25; N, 12.55.

Workup

  1. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-0d3a38a7af9046c69420be9f4bec3a15
Source dataset
uspto-grants-1986_12
Patent number
US04628094

Reaction notes

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