Tetrafluoroboric acid → HCID 86668286, compound

HRID 1618870Notes

Reaction equation

HRID 1618870 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([CH:17]=[CH:18][C:19]2[C:20]([CH3:32])([CH3:31])[O:21][C:22](=[C:26]([C:29]#[N:30])[C:27]#[N:28])[C:23]=2[C:24]#[N:25])=[CH:13][C:3]=1[O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].[N:33]([O-])=O.[Na+].[F:37][B-:38]([F:41])([F:40])[F:39].[H+]>O>[F:37][B-:38]([F:41])([F:40])[F:39].[C:10]([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][O:4][C:3]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]2[C:20]([CH3:32])([CH3:31])[O:21][C:22](=[C:26]([C:29]#[N:30])[C:27]#[N:28])[C:23]=2[C:24]#[N:25])[CH:15]=[CH:16][C:2]=1[N+:1]#[N:33])([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 23668193Sodium NitriteHCID 86638780HCID 86638780, compound

Product 1

HCID 86668286HCID 86668286, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 6-{2-amino-5-[2-(4-cyano-5-dicyanomethylene-2,2-dimethyl-2,5-dihydro-furan-3-yl)-vinyl]-phenoxy}-hexanoic acid (0.30 g, 0.69 mmol) at 5° C. in 3.2 mls of fluoroboric acid (60%) was added a solution of sodium nitrite (0.29 g, 4.27 mmol) in 2 mls of water. The cooling bath was removed and the mixture was allowed to stir at room temperature for 2 hours. The resulting yellow solid, 2-(5-carboxy-pentyl oxy)-4-[2-(4-cyano-5-dicyanomethylene-2,2-dimethyl-2,5-dihydro-furan-3-yl)-vinyl]-benzenediazonium tetrafluoroborate, was removed by vacuum filtration and air dried (0.35 g, 97%). 1H NMR (400 MHz, DMSO) δ: 8.66 (d, 1H, J=8.4 Hz), 8.07 (s, 1H), 7.97 (d, 1H, J=9.2 Hz), 7.86 (d, 1H, J=16.4 Hz), 7.55 (d, 1H, J=16.4 Hz), 4.52 (t, 2H, J=6.4 Hz), 2.27 (t, 2H, J=7.2 Hz), 1.86 (m, 2H), 1.83 (s, 6H), 1.61 (m, 2H), 1.53 (m, 2H). IR (neat): 2360, 2341, 2264, 2230, 1730, 1586, 1481, 1307, 1106.

Workup

  1. customThe cooling bath was removed
  2. customThe resulting yellow solid, 2-(5-carboxy-pentyl oxy)-4-[2-(4-cyano-5-dicyanomethylene-2,2-dimethyl-2,5-dihydro-furan-3-yl)-vinyl]-benzenediazonium tetrafluoroborate, was removed by vacuum filtration and air
  3. customdried (0.35 g, 97%)

Sources & evidence

ORD record
ord-ea30ce304ba84c16a8c73474cf29237b
Source dataset
uspto-grants-2014_07
Patent number
US08772048B2

Reaction notes

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