Azido(trimethyl)stannane → HCID 178456811, compound

HRID 397134Notes

Reaction equation

HRID 397134 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[NH: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]([NH: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 15654687HCID 15654687, compound

Product 1

HCID 178456811HCID 178456811, compoundYield 758.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of ethyl 1-[(2′-cyanobiphenyl-4-yl)methyl]-2-propylaminobenzimidazole-7-carboxylate (1.20 g) and trimethyltin azide (2.7 g) in toluene (15 ml) was heated for 50 hours under reflux. Precipitates were collected by filtration and suspended in methanol (20 ml). After addition of 1N—HCl (15 ml), the reaction mixture was stirred at room temperature for 10 minutes. The mixture was adjusted to about pH 5 with 1N—NaOH, followed by extraction 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 give crystals. Recrystallization from methanol-ethyl acetate gave colorless crystals (10 g, 77%), m.p. 170-172° C.

Workup

  1. temperatureunder reflux
  2. customPrecipitates
  3. filtrationwere collected by filtration
  4. additionAfter addition of 1N—HCl (15 ml)
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer was washed with water
  7. customdried
  8. concentrationconcentrated to dryness
  9. customThe concentrate was purified by column chromatography on silica gel
  10. customto give crystals
  11. customRecrystallization from methanol-ethyl acetate

Sources & evidence

ORD record
ord-ec1c792acbf645d28ba40c10100d5b9b
Source dataset
uspto-grants-2003_08
Patent number
US06608210B2

Reaction notes

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