Hydrochloric Acid → HCID 67021617, compound

HRID 1010718Notes

Reaction equation

HRID 1010718 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[N:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][CH:13]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl>C1(C)C(C)=CC=CC=1.[OH-].[Na+].C(=C/C(/C=C/C1C=CC=CC=1)=O)\C1C=CC=CC=1>[N:12]1([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[CH:13]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 13181,10-PhenanthrolineHCID 5798BenzimidazoleHCID 10796Cesium carbonateHCID 1372144-Iodophenylacetic acid

Product 1

HCID 67021617HCID 67021617, compoundYield 84.5%

Reagents, catalysts & solvents 3

HCID 640180(1E,4E)-1,5-Diphenyl-1,4-pentadien-3-oneCatalystHCID 7237O-XyleneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 4.4 g of 4-iodophenylacetic acid, 2.98 g of benzoimidazole, 197 mg of trans,trans-dibenzylideneacetone, 3.33 g of 1,10-phenanthroline, 211 mg of copper (I) trifluoromethanesulfonate benzene complex and 6 g of Cs2CO3 in 12 ml of xylene is stirred for 88 hours at 125° C. The mixture obtained is allowed to cool to rt and concentrated in vacuo. The concentration residue obtained is dissolved in 1N NaOH aqueous solution and the mixture obtained is extracted with EtOAc. The pH of the aqueous layer obtained is adjusted to acidic pH by addition of 1N HCl aqueous solution. A precipitate forms and is collected by vacuum filtration (batch 1) is collected by vacuum filtration. The aqueous phase from the filtrate obtained is extracted with CH2Cl2. The organic phase is dried (Na2SO4), filtered and concentrated. The concentration residue obtained (batch 2) is combined with batch 1 and triturated in Et2O. 3.58 g of (4-benzoimidazol-1-yl-phenyl)-acetic acid are obtained.

Workup

  1. customThe mixture obtained
  2. temperatureto cool to rt
  3. concentrationconcentrated in vacuo
  4. customThe concentration residue obtained
  5. customthe mixture obtained
  6. extractionis extracted with EtOAc
  7. customThe pH of the aqueous layer obtained
  8. filtrationA precipitate forms and is collected by vacuum filtration (batch 1)
  9. filtrationis collected by vacuum filtration
  10. customThe aqueous phase from the filtrate obtained
  11. extractionis extracted with CH2Cl2
  12. dry with materialThe organic phase is dried (Na2SO4)
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customThe concentration residue obtained (batch 2)
  16. customtriturated in Et2O

Sources & evidence

ORD record
ord-91e6258dec0a4b6aa63f7a44459051c4
Source dataset
uspto-grants-2011_07
Patent number
US07977338B2

Reaction notes

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