Acetonitrile → HCID 16045798, compound

HRID 1410185Notes

Reaction equation

HRID 1410185 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=2)[N:8]=[C:7]1[NH2:20].C(#N)C.NN.C(OC(=O)C)C>CO.[Fe](Cl)(Cl)Cl>[NH2:17][C:13]1[CH:12]=[C:11]([C:9]2[N:8]=[C:7]([NH2:20])[N:6]([CH2:5][C:4]3[CH:21]=[CH:22][CH:23]=[CH:24][C:3]=3[O:2][CH3:1])[CH:10]=2)[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 8857Ethyl AcetateHCID 9321HydrazineHCID 67114100HCID 67114100, compound

Product 1

HCID 16045798HCID 16045798, compound

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 887MethanolSolvent

Procedure

51.1 A mixture of 2.5 g 1-(2-methoxybenzyl)-4-(3-nitrophenyl)-1H-imidazole-2-ylamine (7.7 mmol, Example 45), 2.5 g activated carbon, 30 mg iron(III) chloride (in the form of the hexahydrate) in 100 mL methanol, and 20 mL acetonitrile was heated at reflux, slowly combined with 50 mL hydrazine, and then stirred for an additional 2 hr under reflux. The batch was filtered, concentrated, taken up in acetic ethyl ester, extracted with water, and the organic phase was dried (Na2SO4) and concentrated. The residue thus obtained was mixed with acetic ethyl ester, suctioned off, and dried (2 g target product).

Workup

  1. temperatureat reflux
  2. temperatureunder reflux
  3. filtrationThe batch was filtered
  4. concentrationconcentrated
  5. extractionextracted with water
  6. dry with materialthe organic phase was dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe residue thus obtained
  9. customdried (2 g target product)

Sources & evidence

ORD record
ord-6bd0d83f9f804ea4921f725784e7f375
Source dataset
uspto-grants-2014_12
Patent number
US08921406B2

Reaction notes

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