Dichloromethane → HCID 45381426, compound

HRID 1402824Notes

Reaction equation

HRID 1402824 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([NH2:9])[CH:3]=1.[C:10]1([CH:20]2[CH2:26][C:25](=O)[O:24][C:22](=[O:23])[CH2:21]2)[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1.[Cl:28]CCl>Cl.O1CCOCC1>[ClH:28].[I:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:25]([CH2:26][CH:20]([C:10]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH:13]=[CH:12][CH:11]=3)[CH2:21][C:22]([OH:24])=[O:23])[NH:9][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 112070494-Iodobenzene-1,2-diamineHCID 54485229HCID 54485229, compound

Product 1

HCID 45381426HCID 45381426, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Iodo-1,2-phenylenediamine (0.47 g) and 3-(1-naphthyl)glutaric anhydride (0.48 g) were dissolved in dichloromethane (6 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 (0.69 g) as beige coloured solid. This solid was dissolved in 4M HCl in 1,4-dioxane (3 ml) and the dark solution was heated to reflux for 1 h. All volatiles were removed at the water aspirator and the amorphous residue is crystallised from acetone/methanol to provide 4-(5-iodo-2-benzimidazolyl)-3-(1-naphthyl)butanoic acid HCl (0.54 g) as light grey 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. customAll volatiles were removed at the water aspirator
  10. customthe amorphous residue is crystallised from acetone/methanol

Sources & evidence

ORD record
ord-575bd0a2a4944de1b140f28129ab5a35
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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