Azidotrimethylsilane → 714-95-4

HRID 926099Notes

Reaction equation

HRID 926099 reaction equation
C[Si]([N:5]=[N+:6]=[N-:7])(C)C.F[B-](F)(F)F.[F:13][S:14]([F:26])([F:25])([F:24])([F:23])[C:15]1[CH:20]=[CH:19][C:18]([N+]#N)=[CH:17][CH:16]=1>>[F:13][S:14]([F:23])([F:24])([F:25])([F:26])[C:15]1[CH:16]=[CH:17][C:18]([N:5]=[N+:6]=[N-:7])=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 1222352754-(Pentafluorosulfanyl)phenyldiazonium Tetrafluoroborate

Product 1

HCID 102367698714-95-4Yield 86.4%

Procedure

(Sheppard, J. Am. Chem. Soc. 1962, 84, 3064-3072) Trimethylsilyl azide (6.5 mg, 0.056 mmol) was added to a solution of 1 (10.2 mg, 0.0321 mmol) in [BMIM][BF4] (65.0 mg). After stirring for 5 min, the mixture was extracted with hexane (0.5 mL×3) and the combined extracts was evaporated to give pure 25a as a colorless oil (6.8 mg, 86%): IR (ATR): {tilde over (v)}=2124, 2099, 1586, 1501, 1287, 843 cm−1. MS (GC, EI): m/z=245 [M+], 219 [M+-CN], 200 [M+-CFN], 111. 1H NMR (500 MHz, CDCl3): δ=7.74 (d, J=9.0 Hz, 2H), 7.08 (d, J=9.0 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3): δ=150.3 (C), 143.3 (C), 127.7 (2CH), 118.9 (2CH) ppm. 19F NMR (470 MHz, CDCl3): δ=84.4 (quint, J=150 Hz, 1 F), 63.5 (d, J=150 Hz, 4 F) ppm.

Workup

  1. extractionthe mixture was extracted with hexane (0.5 mL×3)
  2. customthe combined extracts was evaporated

Sources & evidence

ORD record
ord-90c2655b54a14668a74869b147d9728b
Source dataset
uspto-grants-2016_03
Patent number
US09284336B1

Reaction notes

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