Bis-(1H-imidazol-2-YL)-methanone → HCID 59333331, compound

HRID 1893489Notes

Reaction equation

HRID 1893489 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)[C:12]([NH2:20])=[CH:11][C:10]=1[C:21]([F:24])([F:23])[F:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25](C1NC=CN=1)(C1NC=CN=1)=[O:26]>ClC1C=CC=CC=1Cl>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]2[C:12]([NH:20][C:25](=[O:26])[C:16]3[N:15]2[CH:19]=[CH:18][N:17]=3)=[CH:11][C:10]=1[C:21]([F:24])([F:22])[F:23])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 59333338HCID 59333338, compound

Product 1

HCID 59333331HCID 59333331, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of N-benzyl-5-(1H-imidazol-1-yl)-2-(trifluoromethyl)benzene-1,4-diamine (160 mg; 0.48 mmol; 1 eq) and carbonyl diimidazole (156 mg; 0.96 mmol; 2 eq) in 1,2-dichlorobenzene (20 ml) is stirred under argon at reflux for 3 h. Concentration, filtration over a small silicagel pad with ethyl acetate as eluent and purification by prep CCM on silicagel (ethyl acetate) affords the title product (72 mg; 0.2 mmol; 42%) as a pale yellow solid.

Workup

  1. temperatureat reflux for 3 h
  2. concentrationConcentration, filtration over a small silicagel pad with ethyl acetate as eluent
  3. custompurification by prep CCM on silicagel (ethyl acetate)

Sources & evidence

ORD record
ord-ab95f038c89f43268a5fa80a1d48d3cd
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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