Hydrochloric Acid → HCID 45381428, compound

HRID 1402788Notes

Reaction equation

HRID 1402788 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[NH2:16])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH:24]2[CH2:30][C:29](=O)[O:28][C:26](=[O:27])[CH2:25]2)=[CH:20][CH:19]=1.Cl>O1CCOCC1>[ClH:17].[C:5]([C:4]1[CH:13]=[CH:14][C:15]2[N:16]=[C:29]([CH2:30][CH:24]([C:21]3[CH:20]=[CH:19][C:18]([Cl:17])=[CH:23][CH:22]=3)[CH2:25][C:26]([OH:28])=[O:27])[NH:1][C:2]=2[CH:3]=1)(=[O:6])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1046394-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dioneHCID 1355203,4-Diaminobenzophenone

Product 1

HCID 45381428HCID 45381428, compoundYield 140.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The solution of commercial 3,4-diaminobenzophenone (0.43 g) and 3-(4-chlorophenyl)glutaric anhydride (0.45 g) in 1,4-dioxane (3 ml) was stirred under reflux for 0.5 h. 4M HCl in 1,4-dioxane (3 ml) was added and the solution is further heated to reflux for 2.5 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 (0.64 g) as light brown solid.

Workup

  1. temperatureunder reflux for 0.5 h
  2. temperaturethe solution is further heated
  3. temperatureto reflux for 2.5 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-9c89ad6d96cc4ea287a2b4cc086aa473
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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