Sodium hydride → HCID 178458913, compound

HRID 612767Notes

Reaction equation

HRID 612767 reaction equation
[H-].[Na+].[CH2:3]([O:6][C:7]1[NH:8][C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:4][CH3:5].C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[N:23]2[C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]3[CH:39]=[CH:38][C:37]([CH2:40]Br)=[CH:36][CH:35]=3)=[N:26][N:25]=[N:24]2)C=CC=CC=1>CN(C=O)C>[CH2:3]([O:6][C:7]1[N:8]([CH2:40][C:37]2[CH:38]=[CH:39][C:34]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[C:27]3[NH:23][N:24]=[N:25][N:26]=3)=[CH:35][CH:36]=2)[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 30406051H-Benzimidazole, 2-propoxy-HCID 100534615-(4'-(Bromomethyl)(1,1'-biphenyl)-2-yl)-1-trityl-1H-tetraazole

Product 1

HCID 178458913HCID 178458913, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.24 g) was added to a stirred solution of 2-propoxybenzimidazole (0.71 g) in DMF (10 ml) under ice-cooling. The mixture was stirred for 20 minutes, to which was added N-triphenylmethyl-5-(4'-bromomethylbiphenyl-2-yl) tetrazole (2.3 g), followed by stirring at room temperature for 5 hours. To the reaction mixture was added ice-water, the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried and concentrated to dryness. The concentrate was dissolved in methanol (50 ml), to which was added 1N-HCl (15 ml), followed by stirring at 60° C. for 2 hours. The reaction mixture was concentrated, to which were added water (15 ml) and ethyl acetate (15 ml). The mixture was made alkaline with 1N NaOH and shaken. The aqueous layer was adjusted to pH 3-4 with 1N-HCl and then extracted with chloroform. The organic layer was washed with water, dried and concentrated to dryness. The concentrate was purified by column chromatography on silica gel to yield crystals. Recrystallization from ethyl acetate--methanol gave colorless crystals (0.58 g, 35%), m.p. 177-179° C. (decomp.).

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 5 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated to dryness
  7. dissolutionThe concentrate was dissolved in methanol (50 ml), to which
  8. additionwas added 1N-HCl (15 ml)
  9. stirringby stirring at 60° C. for 2 hours
  10. concentrationThe reaction mixture was concentrated, to which
  11. additionwere added water (15 ml) and ethyl acetate (15 ml)
  12. stirringshaken
  13. extractionextracted with chloroform
  14. washThe organic layer was washed with water
  15. customdried
  16. concentrationconcentrated to dryness
  17. customThe concentrate was purified by column chromatography on silica gel
  18. customto yield crystals
  19. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-e7afebea9ebc4e028e9841fdc6768b6e
Source dataset
uspto-grants-1999_12
Patent number
US06004989

Reaction notes

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