Azido(trimethyl)stannane → HCID 178458916, compound

HRID 1760871Notes

Reaction equation

HRID 1760871 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]-2propoxybenzimidazole-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-f8f7046942574816b585e321a1ae96bd
Source dataset
uspto-grants-2005_01
Patent number
US06844443B2

Reaction notes

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