Ammonium thiocyanate → HCID 125492223, compound

HRID 591371Notes

Reaction equation

HRID 591371 reaction equation
[S-:1][C:2]#[N:3].[NH4+].F[B-](F)(F)F.[F:10][S:11]([F:23])([F:22])([F:21])([F:20])[C:12]1[CH:17]=[CH:16][C:15]([N+]#N)=[CH:14][CH:13]=1>CC#N>[F:10][S:11]([F:20])([F:21])([F:22])([F:23])[C:12]1[CH:13]=[CH:14][C:15]([S:1][C:2]#[N:3])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 15666Ammonium thiocyanateHCID 1222352754-(Pentafluorosulfanyl)phenyldiazonium Tetrafluoroborate

Product 1

HCID 125492223HCID 125492223, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ammonium thiocyanate (7.3 mg, 0.096 mmol) and 1 (10.1 mg, 0.0318 mmol) in 0.29 g of MeCN was heated at 70° C. for 0.5 h. After cooling, the mixture was filtered through SiO2 with CH2Cl2 and the solvent was evaporated to give a pale yellow oil, whose purification by SiO2 column chromatography with 9:1 hexane/CH2Cl2 furnished pure 25c as colorless crystals (2.6 mg, 31%); m.p. 67.2-68.2° C. IR (ATR): {tilde over (v)}=3103, 2162, 1585, 1479, 1402, 1105, 1082, 837 cm-1. MS (GC, EI): m/z=261 [M+], 242 [M+-F], 153, 133. 1H NMR (500 MHz, CDCl3): δ=7.84 (d, J=8.8 Hz, 2H), 7.61 (d, J=8.8 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3): δ=154.0 (C), 129.6 (C), 128.7 (2CH), 127.8 (2CH), 108.6 (C) ppm. 19F NMR (470 MHz, CDCl3): δ=82.5 (quint, J=151 Hz, 1 F), 62.9 (d, J=151 Hz, 4 F) ppm.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through SiO2 with CH2Cl2
  3. customthe solvent was evaporated
  4. customto give
  5. customa pale yellow oil, whose purification by SiO2 column chromatography with 9:1 hexane/CH2Cl2 furnished pure 25c as colorless crystals (2.6 mg, 31%)

Sources & evidence

ORD record
ord-38abaa7185ef43c8931687017a397458
Source dataset
uspto-grants-2016_01
Patent number
US09238660B1

Reaction notes

Loading…