Methyl iodide → 2-(1-trityl-1H-imidazol-4-yl)-propionitrile

HRID 2380821Notes

Reaction equation

HRID 2380821 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][C:26]#[N:27])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28]I.[H-].[Na+]>C1COCC1>[C:1]([N:20]1[CH:24]=[C:23]([CH:25]([CH3:28])[C:26]#[N:27])[N:22]=[CH:21]1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19099310HCID 19099310, compound

Product 1

HCID 688727612-(1-trityl-1H-imidazol-4-yl)-propionitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-5 °C

Procedure

9.2 g (1-trityl-1H-imidazol-4-yl)-acetonitrile are dissolved in 120 mL THF, the solution is cooled to −5° C. and 1.8 mL methyl iodide and 1.08 g sodium hydride (60%) are added. The suspension is stirred for 12 h at RT and then applied directly to RP gel and purified by RP chromatography (C18, 10/90 to 90/10 acetonitrile/water in 15 min-0.2% formic acid is added to both solvents).

Workup

  1. custompurified by RP chromatography (C18, 10/90 to 90/10 acetonitrile/water in 15 min-0.2% formic acid
  2. additionis added to both solvents)

Sources & evidence

ORD record
ord-ae61ec25668d49029fa6ea575e3d2220
Source dataset
uspto-grants-2012_09
Patent number
US08258129B2

Reaction notes

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