Trimethylsilyl iodide → HCID 18947721, compound

HRID 1769300Notes

Reaction equation

HRID 1769300 reaction equation
I[Si](C)(C)C.C(OC([NH:13][C:14]1[N:15]=[C:16]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[NH:17][C:18]=1[C:19]#[N:20])=O)(C)(C)C>C(#N)C>[NH2:13][C:14]1[N:15]=[C:16]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[NH:17][C:18]=1[C:19]#[N:20]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 18947715HCID 18947715, compound

Product 1

HCID 18947721HCID 18947721, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of iodotrimethylsilane (2.83 g, 0.014 mol) in acetonitrile (5 ml) was added dropwise with stirring to a suspension of 4-(tert.butoxycarbonylamino)-5-cyano-2-(2,4-dichlorophenyl)imidazole (5.0 g, 0.014 mol) in acetonitrile (250 ml) whilst maintaining the temperature at about 0° C. The mixture was stirred at room temperature for 48 hours and the precipitated beige solid filtered off. The solid was purified by mplc on silica eluting with a mixture of ethyl acetate and hexane (1:2) to give an off-white solid which was recrystallized from ethanol to give 4-amino-5-cyano-2-(2,4-dichlorophenyl)imidazole (1.35 g) m.p. 223°-225° C. as an off-white solid.

Workup

  1. filtrationthe precipitated beige solid filtered off
  2. customThe solid was purified by mplc on silica eluting with a mixture of ethyl acetate and hexane (1:2)
  3. customto give an off-white solid which
  4. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-acad7e6f6f1c418fbd78b3b710c6322a
Source dataset
uspto-grants-1995_01
Patent number
US05380865

Reaction notes

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