Aniline → HCID 178507742, compound

HRID 926105Notes

Reaction equation

HRID 926105 reaction equation
F[B-](F)(F)F.[F:6][S:7]([F:19])([F:18])([F:17])([F:16])[C:8]1[CH:13]=[CH:12][C:11]([N+:14]#[N:15])=[CH:10][CH:9]=1.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C>[NH2:20][C:21]1[CH:26]=[CH:25][C:24](/[N:15]=[N:14]/[C:11]2[CH:12]=[CH:13][C:8]([S:7]([F:16])([F:17])([F:18])([F:19])[F:6])=[CH:9][CH:10]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 1222352754-(Pentafluorosulfanyl)phenyldiazonium Tetrafluoroborate

Product 1

HCID 178507742HCID 178507742, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diazonium salt 1 (11.1 mg, 0.0349 mmol) and aniline (32.0 mg, 0.344 mmol) were dissolved in 0.19 g of 95% ethanol. After 20 d, the solution was filtered through Celite 545. Evaporation of the solvent gave an orange oil, which was purified by SiO2 column chromatography (8:2 hexane/ethyl acetate) and following preparative TLC (SiO2, CH2Cl2) afforded 27e as orange crystals (2.5 mg, 22%); m.p. 153.0-154.5° C. IR (ATR): {tilde over (v)}=3417, 2915, 1666, 1628, 1603, 1507, 1398, 1302, 1148, 1092, 834 cm−1. MS (GC, EI): m/z=323 [M+], 197, 120, 94, 65. 1H NMR (500 MHz, CDCl3): δ=7.88-7.82 (m, 6H), 6.76 (d, J=8.8 Hz, 2H), 2.20 (br. s, 1H) ppm. 13C NMR (125 MHz, CDCl3): δ=154.1 (C), 150.5 (C), 145.3 (C), 126.9 (2CH), 125.8 (2CH), 122.2 (2CH), 114.5 (2CH) ppm. 19F NMR (470 MHz, CDCl3): δ=84.4 (quint, J=150 Hz, 1 F), 63.2 (d, J=150 Hz, 4 F) ppm.

Workup

  1. filtrationthe solution was filtered through Celite 545
  2. customEvaporation of the solvent
  3. customgave an orange oil, which
  4. customwas purified by SiO2 column chromatography (8:2 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0eb7ed4a0c5943509b3d1ed7c84cc7ba
Source dataset
uspto-grants-2016_03
Patent number
US09284336B1

Reaction notes

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