Hydrochloric Acid → HCID 86592586, compound

HRID 1868337Notes

Reaction equation

HRID 1868337 reaction equation
C[O:2][CH:3](OC)[C:4]1[NH:5][C:6]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=2)=[C:7]([C:9]2[CH:18]=[CH:17][C:12]3=[N:13][N:14]([CH3:16])[N:15]=[C:11]3[CH:10]=2)[N:8]=1.Cl.O.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:16][N:14]1[N:13]=[C:12]2[CH:17]=[CH:18][C:9]([C:7]3[N:8]=[C:4]([CH:3]=[O:2])[NH:5][C:6]=3[C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=3)=[CH:10][C:11]2=[N:15]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 516892Sodium BicarbonateHCID 69062531HCID 69062531, compound

Product 1

HCID 86592586HCID 86592586, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-[2-Dimethoxymethyl-5-(6-methyl-pyridin-2-yl)-1H-imidazol-4-yl]-2-methyl-2H-benzotriazole (700 mg, 1.92 mmol) was dissolved in 40 ml anhydrous tetrahydrofuran. 6M hydrochloric acid solution in water (3.2 ml, 19.2 mmol) was added. The reaction was refluxed for 3 hours and then cooled to room temperature. Saturated aqueous sodium hydrogen carbonate solution was added until approximately pH 8. The organic solvent was removed by rotary evaporation. The residue was dissolved in water and then extracted three times with chloroform. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated to afford 4-(2-methyl-2H-benzotriazol-5-yl)-5-(6-methyl-pyridin-2-yl)-1H-imidazole-2-carbaldehyde (600 mg, 98% yield) as a brown solid.

Workup

  1. temperatureThe reaction was refluxed for 3 hours
  2. customThe organic solvent was removed by rotary evaporation
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted three times with chloroform
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-07307f068c344d5e888049f5f344844e
Source dataset
uspto-grants-2009_12
Patent number
US07635702B2

Reaction notes

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