Hydrochloric Acid → HCID 18933473, compound

HRID 1598337Notes

Reaction equation

HRID 1598337 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23](O)=[O:24])=[CH:13][CH:12]=2)[C:8]2[C:26]([C:30]([O:32][CH3:33])=O)=[CH:27][CH:28]=[CH:29][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].S(Cl)(Cl)=O.[H-].[Li+].[Al+3].[H-].[H-].[H-].Cl>C(Cl)(Cl)Cl.O1CCCC1>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:23][OH:24])=[CH:15][CH:16]=2)[C:8]2[C:26]([CH2:30][O:32][CH3:33])=[CH:27][CH:28]=[CH:29][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 18693007HCID 18693007, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18933473HCID 18933473, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of methyl 2-butyl-1-[2'-carboxybiphenyl-4-yl]methylbenzimidazole-7-carboxylate (0.44 g) and thionyl chloride (0.15 ml) in chloroform (4 ml) was heated for 30 minutes under reflux with stirring. The reaction mixture was concentrated, and the resulting product was used for the subsequent reaction without purification. A stirred solution of the above product in tetrahydrofuran (6 ml) was added dropwise to a suspension of aluminium lithium hydride (40 mg) in tetrahydrofuran (6 ml) under ice-cooling. The reaction mixture was stirred for one minutes at the same temperature, and to the mixture were added 2N-HCl and, then water, followed by extraction with chloroform. The extract was washed with water and dried (MgSO4), and the solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel to give an oil. Crystallization of this product from isopropyl ether afforded colorless prisms (0.13 g, 31%), m.p.126°-127° C.

Workup

  1. temperaturewas heated for 30 minutes
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated
  4. customthe resulting product was used for the subsequent reaction without purification
  5. temperaturecooling
  6. stirringThe reaction mixture was stirred for one minutes at the same temperature
  7. extractionwater, followed by extraction with chloroform
  8. washThe extract was washed with water
  9. dry with materialdried (MgSO4)
  10. customthe solvent was evaporated in vacuo
  11. customThe residue was purified by column chromatography on silica gel
  12. customto give an oil
  13. customCrystallization of this product from isopropyl ether afforded colorless prisms (0.13 g, 31%), m.p.126°-127° C.

Sources & evidence

ORD record
ord-bb60962cdc744ac8a590b1c9f12030b7
Source dataset
uspto-grants-1998_04
Patent number
US05736555

Reaction notes

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