Hydrochloric Acid → HCID 178494643, compound

HRID 653728Notes

Reaction equation

HRID 653728 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[CH2:29][O:30][CH3:31])=[CH:11][CH:10]=1)#[N:2].C[Sn]([N:36]=[N+:37]=[N-:38])(C)C.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.CO.C(Cl)Cl.O>[CH3:31][O:30][CH2:29][C:17]1[N:16]([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[C:1]3[NH:38][N:37]=[N:36][N:2]=3)=[CH:10][CH:11]=2)[C:20]2[C:21]([C:25]([O:27][CH3:28])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5104973Azido(trimethyl)stannaneHCID 15654666HCID 15654666, compound

Product 1

HCID 178494643HCID 178494643, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 21908982Water methylene chlorideSolvent

Procedure

A mixture of methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-methoxymethylbenzimidazole-7-carboxylate (0.4 g) and trimethyltin azide (1.0 g) in toluene (10 ml) was refluxed for 49 hours. The reaction solution was concentrated to dryness to give a residue and the residue was dissolved in methanol (6 ml) and 1N-HCl (6 ml). The solution was allowed to stir for 3 hours and concentrated to dryness to give a residue. The residue was dissolved in CH2Cl2 -H2O and the mixture was made neutral with 1N-NaOH. The organic layer was washed with H2O, dried and concentrated to dryness to give a residue, which was purified by column chromatography on silica gel to give a crystalline product. Recrystallization from ethyl acetate-isopropylether gave colorless needles (0.3 g, 68%).

Workup

  1. temperaturewas refluxed for 49 hours
  2. concentrationThe reaction solution was concentrated to dryness
  3. customto give a residue
  4. concentrationconcentrated to dryness
  5. customto give a residue
  6. washThe organic layer was washed with H2O
  7. customdried
  8. concentrationconcentrated to dryness
  9. customto give a residue, which
  10. customwas purified by column chromatography on silica gel
  11. customto give a crystalline product
  12. customRecrystallization from ethyl acetate-isopropylether

Sources & evidence

ORD record
ord-bf66b63d99e24b79b50aed19537785a9
Source dataset
uspto-grants-1992_07
Patent number
US05128356

Reaction notes

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