Hydrochloric Acid → HCID 45381424, compound

HRID 1402821Notes

Reaction equation

HRID 1402821 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[C:10]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:15]=[CH:14][C:13]([CH:16]2[CH2:22][C:21](=O)[O:20][C:18](=[O:19])[CH2:17]2)=[CH:12][CH:11]=1.Cl>ClCCl.O1CCOCC1>[ClH:1].[C:10]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:15]=[CH:14][C:13]([CH:16]([CH2:22][C:21]2[NH:9][C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=3[N:8]=2)[CH2:17][C:18]([OH:20])=[O:19])=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 72634-Chloro-1,2-diaminobenzeneHCID 17912068HCID 17912068, compound

Product 1

HCID 45381424HCID 45381424, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Commercial 4-chloro-1,2-phenylenediamine (214 mg) and 3-(biphenyl-4-yl)glutaric anhydride (399 mg) were dissolved in dichloromethane (5 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 (0.48 g) as light brown solid. This solid was dissolved in 1,4-dioxane (1 ml) with heating. 4M HCl in 1,4-dioxane (3 ml) was added and the solution was heated to reflux for 1.5 h. The precipitate formed is isolated by suction filtration and washed with 1,4-dioxane and diethyl ether. The crude (0.4 g) is crystallised from acetic acid to provide 3-(biphenyl-4-yl)-4-(5-chloro-2-benzimidazolyl)butanoic acid HCl (0.27 g) as light brown crystals.

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. temperaturewith heating
  8. temperaturethe solution was heated
  9. temperatureto reflux for 1.5 h
  10. customThe precipitate formed
  11. customis isolated by suction filtration
  12. washwashed with 1,4-dioxane and diethyl ether
  13. customThe crude (0.4 g) is crystallised from acetic acid

Sources & evidence

ORD record
ord-1fa815ab991c46bf8cf83aeaa3ff199d
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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