Sodium Acetate → HCID 14518387, compound

HRID 1723094Notes

Reaction equation

HRID 1723094 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][CH3:11].Cl.Cl.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22](=N)OCC)[CH:17]=1.C([O-])(=O)C.[Na+]>C(O)C>[CH2:9]([N:8]1[C:7]2[CH:6]=[CH:5][C:4]([CH2:12][OH:13])=[CH:3][C:2]=2[N:1]=[C:22]1[C:18]1[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=1)[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 12218259HCID 12218259, compoundHCID 20026577HCID 20026577, compound

Product 1

HCID 14518387HCID 14518387, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(a-4) A mixture of 8 parts of 3-amino-4-(propylamino)benzenemethanol, 14.05 parts of ethyl 3-pyridinecarboximidate dihydrochloride, 9.8 parts of sodium acetate and 96 parts of ethanol was stirred for 16 hours at room temperature. The reaction mixture was evaporated. The residue was dissolved in water and treated with ammonia. The precipitated product was filtered off, washed with water and dissolved in dichloromethane. The organic layer was dried, filtered and evaporated. The residue was washed with 2,2'-oxybispropane, yielding 9.9 parts (84.1%) of 1-propyl-2-(3-pyridinyl)-1H-benzimidazole-5-methanol as a residue (interm. 4).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionThe residue was dissolved in water
  3. additiontreated with ammonia
  4. filtrationThe precipitated product was filtered off
  5. washwashed with water
  6. dissolutiondissolved in dichloromethane
  7. customThe organic layer was dried
  8. filtrationfiltered
  9. customevaporated
  10. washThe residue was washed with 2,2'-oxybispropane

Sources & evidence

ORD record
ord-d54b4e0956d247a0b70b78cee05c6ec7
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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