Azido(trimethyl)stannane → HCID 178458916, compound

HRID 397126Notes

Reaction equation

HRID 397126 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][CH2:28][CH3:29])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[O:30][CH2:31][CH2:32][CH3:33])=[CH:11][CH:10]=1)#[N:2].C[Sn]([N:38]=[N+:39]=[N-:40])(C)C>C1(C)C=CC=CC=1>[CH2:31]([O:30][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:40][N:39]=[N:38][N:2]=3)=[CH:14][CH:13]=2)[C:20]2[C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]=1)[CH2:32][CH3:33]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 15654675HCID 15654675, compound

Product 1

HCID 178458916HCID 178458916, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 1-[(2′-cyanobiphenyl-4-yl)methyl]-2-propoxybenzimidazole-7-carboxylate (0.69 g) and trimethyltin azide (0.7 g) in toluene (15 ml) was heated for 4 days under reflux. The reaction mixture was concentrated to dryness and to the mixture was added methanol (20 ml) and 1N—HCl (10 ml). After stirring at room temperature for 30 minutes, the mixture was adjusted to pH 3-4 with 1N NaOH. After removal of the solvent, the residue was extracted with chloroform-water. The organic layer was washed with water and dried, and the solvent was evaporated to dryness to give a syrup. The syrup was purified by column chromatography on silica gel to give crystals. Recrystallization from ethyl acetate-benzene afforded colorless crystals (0.31 g, 43%), m.p. 157-159° C.

Workup

  1. temperaturewas heated for 4 days
  2. temperatureunder reflux
  3. concentrationThe reaction mixture was concentrated to dryness and to the mixture
  4. additionwas added methanol (20 ml) and 1N—HCl (10 ml)
  5. customAfter removal of the solvent
  6. extractionthe residue was extracted with chloroform-water
  7. washThe organic layer was washed with water
  8. customdried
  9. customthe solvent was evaporated to dryness
  10. customto give a syrup
  11. customThe syrup was purified by column chromatography on silica gel
  12. customto give crystals
  13. customRecrystallization from ethyl acetate-benzene afforded colorless crystals (0.31 g, 43%), m.p. 157-159° C.

Sources & evidence

ORD record
ord-9e62aa45459140bd81886ded3344c155
Source dataset
uspto-grants-2003_08
Patent number
US06608210B2

Reaction notes

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