Azido(trimethyl)stannane → HCID 178441477, compound

HRID 274567Notes

Reaction equation

HRID 274567 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH:21]=[CH:20][CH:19]=[C:18]3[C:22]#[N:23])=[CH:13][CH:12]=2)[C:8]2[C:24]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][CH:26]=[CH:27][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].C[Sn]([N:36]=[N+:37]=[N-:38])(C)C>C1(C)C=CC=CC=1>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH:21]=[CH:20][CH:19]=[C:18]3[C:22]3[NH:38][N:37]=[N:36][N:23]=3)=[CH:15][CH:16]=2)[C:8]2[C:24]([C:28]([O:30][CH3:31])=[O:29])=[CH:25][CH:26]=[CH:27][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 15224470HCID 15224470, compound

Product 1

HCID 178441477HCID 178441477, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 2-butyl-1-[[4-(2-cyano-1-pyrrolyl)phenyl]methyl]benzimidazole-7-carboxylate (2.2 g) and trimethyltin azide (3.3 g) in toluene (35 ml) was heated under reflux for 3 days. After concentration, the residue was dissolved in methanol (40 ml) and 1N hydrochloric acid (20 ml) and the mixture was stirred at room temperature for 15 minutes. The reaction mixture was concentrated to dryness and the residue was extracted with ethyl acetate. The extract was washed with water, dried and evaporated. The residue was purified by column chromatography on silica gel to give crystals which were recrystallized from ethyl acetate to afford colorless crystals (1.8 g, 75%), m.p. 186°-187° C.

Workup

  1. temperatureunder reflux for 3 days
  2. concentrationAfter concentration
  3. dissolutionthe residue was dissolved in methanol (40 ml)
  4. concentrationThe reaction mixture was concentrated to dryness
  5. extractionthe residue was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel
  10. customto give crystals which
  11. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7a44b09808ec4729bd56f59548f852d2
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Reaction notes

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