Hydrochloric Acid → HCID 45381428, compound

HRID 1402789Notes

Reaction equation

HRID 1402789 reaction equation
[N+]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[C:6]([NH2:11])[CH:5]=1)([O-])=O.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]2[CH2:25][C:24](=O)[O:23][C:21](=[O:22])[CH2:20]2)=[CH:15][CH:14]=1.Cl.[O:28]1[CH2:33][CH2:32]OCC1>>[ClH:12].[C:33]([C:4]1[CH:9]=[CH:8][C:7]2[N:10]=[C:24]([CH2:25][CH:19]([C:16]3[CH:15]=[CH:14][C:13]([Cl:12])=[CH:18][CH:17]=3)[CH2:20][C:21]([OH:23])=[O:22])[NH:11][C:6]=2[CH:5]=1)(=[O:28])[C:32]1[CH:8]=[CH:9][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 1046394-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dioneHCID 51117914-Nitro-1,2-phenylenediamine

Product 1

HCID 45381428HCID 45381428, compound

Procedure

The solution of commercial 4-nitro-1,2-phenylenediamine (0.31 g) and 3-(4-chlorophenyl)glutaric anhydride (0.45 g) in 1,4-dioxane (3 ml) was stirred under reflux for 0.75 h. 4M HCl in 1,4-dioxane (3 ml) was added and the solution is further heated to reflux for 1 h. After cooling to rt the precipitate is collected by suction filtration and washed with 1,4-dioxane and diethyl ether. The crude is recrystallised from acetic acid to give 4-(5-benzoyl-2-benzimidazolyl)-3-(4-chlorophenyl)butanoic acid HCl (0.59 g) as beige coloured solid.

Workup

  1. temperatureunder reflux for 0.75 h
  2. temperaturethe solution is further heated
  3. temperatureto reflux for 1 h
  4. filtrationis collected by suction filtration
  5. washwashed with 1,4-dioxane and diethyl ether
  6. customThe crude is recrystallised from acetic acid

Sources & evidence

ORD record
ord-10464be13b1f4aa188d245607e05d229
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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