Hydrochloric Acid → HCID 66759435, compound

HRID 1402936Notes

Reaction equation

HRID 1402936 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[CH:19]1[CH2:25][C:24](=O)[O:23][C:21](=[O:22])[CH2:20]1.[ClH:27]>ClCCl.O1CCOCC1>[ClH:27].[N:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][C:24]=1[CH2:25][CH:19]([C:10]1[CH:11]=[CH:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=1)[CH2:20][C:21]([OH:23])=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7243O-PhenylenediamineHCID 86662458HCID 86662458, compound

Product 1

HCID 66759435HCID 66759435, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

1,2-Phenylenediamine (54 mg) and 3-(2-naphthyl)glutaric anhydride (120 mg) were dissolved in dichloromethane (2 ml) with heating. The solution was stirred at rt for 1 h. The precipitate formed was collected by suction filtration, washed with dichloromethane, and dried to give a mixture of regioisomeric amides (131 mg) as colourless solid. This solid was dissolved in 1,4-dioxane (1 ml) with heating, and 4M HCl in 1,4-dioxane (1 ml) was added. The solution was heated to reflux for 1 h. After removal of the solvent the residue was triturated with acetone to give 4-(2-benzimidazolyl)-3-(2-naphthyl)butanoic acid HCl (100 mg) as colourless solid.

Workup

  1. temperaturewith heating
  2. customThe precipitate formed
  3. filtrationwas collected by suction filtration
  4. washwashed with dichloromethane
  5. customdried
  6. customto give
  7. temperaturewith heating
  8. temperatureThe solution was heated
  9. temperatureto reflux for 1 h
  10. customAfter removal of the solvent the residue
  11. customwas triturated with acetone

Sources & evidence

ORD record
ord-01533c0861f143c59394443e4949d344
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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