4-Chloro-1,2-diaminobenzene → HCID 45381887, compound

HRID 1402937Notes

Reaction equation

HRID 1402937 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[CH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][C:11]=1[CH:20]1[CH2:26][C:25](=O)[O:24][C:22](=[O:23])[CH2:21]1>ClCCl.Cl.O1CCOCC1>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:25]([CH2:26][CH:20]([C:11]3[CH:12]=[CH:13][C:14]4[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:10]=3)[CH2:21][C:22]([OH:24])=[O:23])[NH:9][C:4]=2[CH:3]=1

Participants

6

Reactant 2

HCID 72634-Chloro-1,2-diaminobenzeneHCID 86662458HCID 86662458, compound

Product 1

HCID 45381887HCID 45381887, compoundYield 68.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Chloro-1,2-phenylenediamine (143 mg) and 3-(2-naphthyl)glutaric anhydride (240 mg) were dissolved in dichloromethane (3 ml) with heating. The dark solution was stirred at rt for 1 h. The precipitate formed was collected by suction filtration, washed with dichloromethane, and dried in vacuo to give a mixture of regioisomeric amides (0.32 g) as brownish solid. This solid was dissolved in 4M HCl in 1,4-dioxane (4 ml) and the dark solution was heated to reflux for 1 h. After removal of the solvent in vacuo the residue was taken up in acetic acid (5 ml), treated with charcoal, and filtered. From the filtrate the solvent was removed and the residue triturated with acetone to give 4-(5-chloro-2-benzimidazolyl)-3-(2-naphthyl)butanoic acid HCl (138 mg) as colourless solid.

Workup

  1. temperaturewith heating
  2. customThe precipitate formed
  3. filtrationwas collected by suction filtration
  4. washwashed with dichloromethane
  5. customdried in vacuo
  6. customto give
  7. temperaturethe dark solution was heated
  8. temperatureto reflux for 1 h
  9. customAfter removal of the solvent in vacuo the residue
  10. additiontreated with charcoal
  11. filtrationfiltered
  12. customFrom the filtrate the solvent was removed
  13. customthe residue triturated with acetone

Sources & evidence

ORD record
ord-194d2e8a6cdc4be4b2ad8d06e59c7aa6
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

Loading…