Dichloromethane → HCID 66759302, compound

HRID 1402826Notes

Reaction equation

HRID 1402826 reaction equation
[I: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.[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: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 3

HCID 6344DichloromethaneHCID 112070494-Iodobenzene-1,2-diamineHCID 86662458HCID 86662458, compound

Product 1

HCID 66759302HCID 66759302, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Iodo-1,2-phenylenediamine (0.47 g) and 3-(2-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 (0.82 g) as light red 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. The precipitate formed is isolated by suction filtration of the still hot mixture and washed with 1,4-dioxane, hot acetic acid, and finally diethyl ether to provide 4-(5-iodo-2-benzimidazolyl)-3-(2-naphthyl)butanoic acid HCl (0.71 g) as light red 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. customThe precipitate formed
  10. customis isolated by suction filtration of the still hot mixture
  11. washwashed with 1,4-dioxane, hot acetic acid, and finally diethyl ether

Sources & evidence

ORD record
ord-e3cc08723f564ddbb764253033812ff5
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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