Azido(trimethyl)stannane → HCID 178467365, compound

HRID 612788Notes

Reaction equation

HRID 612788 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[O:29][CH2:30][CH3:31])=[CH:11][CH:10]=1)#[N:2].C[Sn]([N:36]=[N+:37]=[N-:38])(C)C>C1(C)C=CC=CC=1>[CH2:30]([O:29][C:17]1[N:16]([CH2:15][C:12]2[CH:11]=[CH:10][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:14][CH:13]=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)[CH3:31]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 15654674Methyl 1-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate

Product 1

HCID 178467365HCID 178467365, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxybenzimidazole-7-carboxylate (1.85 g) and trimethyltin azide (2.80 g) in toluene (15 ml) were heated under reflux for one day. The reaction mixture was concentrated to dryness. To the residue were added methanol (50 ml) and 1N-HCl (20 ml) and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was adjusted to about pH 3-4 with 1N-NaOH. After removal of the solvent, the residual syrup was purified by column chromatography on silica gel to give crystals. Recrystallization from ethyl acetate--benzene gave colorless crystals (1.16 g, 56%), m.p. 191-193° C. (decomp.).

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for one day
  3. concentrationThe reaction mixture was concentrated to dryness
  4. additionTo the residue were added methanol (50 ml) and 1N-HCl (20 ml)
  5. customAfter removal of the solvent
  6. customthe residual syrup was purified by column chromatography on silica gel
  7. customto give crystals
  8. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-12c66528b2884487b80e0c6f11d227b6
Source dataset
uspto-grants-1999_12
Patent number
US06004989

Reaction notes

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