Imidazole → HCID 46946382, compound

HRID 1470625Notes

Reaction equation

HRID 1470625 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([NH2:18])=O)[C:9]=3[N:8]=2)=[CH:3][CH:2]=1.N1C=CN=C1.P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:1]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=[CH:5][C:4]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]#[N:18])[C:9]=3[N:8]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24813Phosphorus oxychlorideHCID 45484114HCID 45484114, compound

Product 1

HCID 46946382HCID 46946382, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-30 °C

Procedure

To the solution of 2-biphenyl-4-yl-1H-benzoimidazole-4-carboxylic acid amide (0.24 g, 0.76 mmol) in pyridine (10 mL) was added imidazole (0.11 g, 1.53 mmol). The reaction mixture was cooled to −30° C. and phosphorous oxy chloride (0.3 mL, 3.1 mmol) was added drop wise. The reaction mixture was then stirred at −10° C. for 4 h. Progress of the reaction was monitored by TLC. The reaction mixture was concentrated to dryness and water was added. This mixture was extracted with ethyl acetate and the combined organic layers were concentrated. The resulting residue was purified by column chromatography using 30% ethyl acetate in hexane to get the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness and water
  2. additionwas added
  3. extractionThis mixture was extracted with ethyl acetate
  4. concentrationthe combined organic layers were concentrated
  5. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-6d7510080f8d400b82c5f09f0f3537ea
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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