Imidazole → HCID 68156808, compound

HRID 1892715Notes

Reaction equation

HRID 1892715 reaction equation
II.O[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1/[N:11]=[N:12]/[C:13]1[C:18]([CH3:19])=[CH:17][C:16]([OH:20])=[CH:15][C:14]=1[CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1>O1CCCC1>[N:11]1[N:12]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([OH:20])=[CH:15][C:14]=2[CH3:21])[CH:4]=[C:5]2[C:6]=1[CH:7]=[CH:8][CH:9]=[CH:10]2

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 178429017HCID 178429017, compound

Product 1

HCID 68156808HCID 68156808, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Iodine (3980 mg, 15.7 mmol) was added to the orange solution of (E)-4-((2-(hydroxymethyl)phenyl)diazenyl)-3,5-dimethylphenol (2680 mg, 10.46 mmol), triphenylphosphine (4110 mg, 15.7 mmol) and imidazole (2140 mg, 31.4 mmol) in tetrahydrofuran (30 mL) at room temperature. The mixture was stirred for 40 minutes. The solvent was evaporated. The crude was dissolved in EtOAc/MeOH and loaded to the column and purified by ISCO (40 g silica gel, EtOAc/heptane: 0→50%), leading to the desired product as a white/pale yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.85 (s, 6H) 6.49 (s, 2H) 7.07-7.21 (m, 1H) 7.32-7.42 (m, 1H) 7.75 (d, J=8.58 Hz, 1H) 7.80 (dd, J=8.78, 0.98 Hz, 1H) 7.96 (d, J=0.78 Hz, 1H) 7.99 (s, 1H). LCMS: m/z=239.2 [M+H].

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe crude was dissolved in EtOAc/MeOH
  3. custompurified by ISCO (40 g silica gel, EtOAc/heptane: 0→50%)

Sources & evidence

ORD record
ord-14e26af8ea3f408c82851d7f2601b4f7
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

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