HCID 15428582, compound → HCID 18779748, compound

HRID 1421714Notes

Reaction equation

HRID 1421714 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[N:10]=[CH:11][N:12](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:13]=2)=[CH:4][CH:3]=1.[O:33]=[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]1[C:40]1[CH:47]=[CH:46][C:43]([CH2:44]Br)=[CH:42][CH:41]=1>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[N:10]([CH2:44][C:43]3[CH:46]=[CH:47][C:40]([N:35]4[CH:36]=[CH:37][CH:38]=[CH:39][C:34]4=[O:33])=[CH:41][CH:42]=3)[CH:11]=[N:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 15428582HCID 15428582, compoundHCID 18698776HCID 18698776, compound

Product 1

HCID 18779748HCID 18779748, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-(4-bromophenyloxy)-1-trityl-1H-imidazole (0.345 g, 0.72 mmol) and the bromide from Example 1, Step 3 (0.19 g, 0.72 mmol) in anhydrous acetonitrile (10 mL) was heated under reflux at 60° C. for 24 h. The resultant solution was concentrated, and the residue dissolved in methanol. The methanolic solution was heated under reflux for 3 h, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 1:1 v/v 5% methanol in chloroform and chloroform saturated with ammonia gas. Collection and concentration of appropriate fractions provide the titled compound.

Workup

  1. concentrationThe resultant solution was concentrated
  2. dissolutionthe residue dissolved in methanol
  3. temperatureThe methanolic solution was heated
  4. temperatureunder reflux for 3 h
  5. concentrationconcentrated under vacuum
  6. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-8d705703417d441889ea29f022b88159
Source dataset
uspto-grants-2000_06
Patent number
US06077853

Reaction notes

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