Azido(trimethyl)stannane → HCID 178441475, compound

HRID 274581Notes

Reaction equation

HRID 274581 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:18]([C:23]#[N:24])=[N:19][CH:20]=[N:21][CH:22]=3)=[CH:13][CH:12]=2)[C:8]2[C:25]([C:29]([O:31][CH3:32])=[O:30])=[CH:26][CH:27]=[CH:28][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].C[Sn]([N:37]=[N+:38]=[N-:39])(C)C>C1(C)C=CC=CC=1>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:18]([C:23]4[NH:39][N:38]=[N:37][N:24]=4)=[N:19][CH:20]=[N:21][CH:22]=3)=[CH:13][CH:12]=2)[C:8]2[C:25]([C:29]([O:31][CH3:32])=[O:30])=[CH:26][CH:27]=[CH:28][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 20092964HCID 20092964, compound

Product 1

HCID 178441475HCID 178441475, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 2-butyl-1-[p-(4-cyanopyrimidin-5-yl)benzyl]benzimidazole-7-carboxylate (0.18 g, 0.4 mmol) and trimethyltin azide (0.27 g, 1.3 mmol) in toluene (5 ml) was heated under reflux for 28 hours. After removal of the solvent by evaporation, the residue was purified by column chromatography on silica gel. Recrystallization from ethyl acetate-isopropyl ether afforded colorless powders (40 mg, 20%), m.p. 215°-220° C.

Workup

  1. temperatureunder reflux for 28 hours
  2. customAfter removal of the solvent
  3. customby evaporation
  4. customthe residue was purified by column chromatography on silica gel
  5. customRecrystallization from ethyl acetate-isopropyl ether afforded colorless powders (40 mg, 20%), m.p. 215°-220° C.

Sources & evidence

ORD record
ord-0a445d2f678a479ab79078e0ca437c86
Source dataset
uspto-grants-1995_02
Patent number
US05389641

Reaction notes

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