Tributyltin Chloride → HCID 178439891, compound

HRID 1974448Notes

Reaction equation

HRID 1974448 reaction equation
[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH2:12][CH3:13])[N:7]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]#[N:28])=[N:19][CH:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[N-:29]=[N+:30]=[N-:31].[Na+].C([Sn](Cl)(CCCC)CCCC)CCC>>[CH3:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][CH2:12][CH3:13])[N:7]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]4[NH:31][N:30]=[N:29][N:28]=4)=[N:19][CH:20]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 15096Tributyltin ChlorideHCID 33557Sodium AzideHCID 19383099HCID 19383099, compound

Product 1

HCID 178439891HCID 178439891, compoundYield 46%

Procedure

A mixture of 4-methyl-2-propyl-1-[[2-(2-cyanophenyl)-5-pyridinyl]methyl]-1H-benzimidazol (0.87 g, 2.39 mmol), NaN3 (0.77 g, 11.94 mmol), and tri-n-butyltin chloride (3.88 g, 11.94 mmol) in xylenes (20 mL) was heated under reflux for 20 h. The reaction mixture was concentrated and 2N HCl was added. The mixture was extracted with ether (discarded) and adjusted to pH 5 with 50% NaOH. The aqueous phase was extracted with CH2Cl2, and the extracts were washed with water, dried, and concentrated. Purification by flash chromatography (5% MeOH/CH2Cl2) and recrystallization from EtOH/EtOAc/ether gave 0.45 g (45%) of product as a white solid, mp 169°-170° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 h
  3. concentrationThe reaction mixture was concentrated
  4. addition2N HCl was added
  5. extractionThe mixture was extracted with ether (discarded)
  6. extractionThe aqueous phase was extracted with CH2Cl2
  7. washthe extracts were washed with water
  8. customdried
  9. concentrationconcentrated
  10. customPurification
  11. customby flash chromatography (5% MeOH/CH2Cl2) and recrystallization from EtOH/EtOAc/ether

Sources & evidence

ORD record
ord-67351282ea5f43618fd5be58b87dd17d
Source dataset
uspto-grants-1994_02
Patent number
US05283242

Reaction notes

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