Tributyltin Chloride → HCID 178439872, compound

HRID 2399689Notes

Reaction equation

HRID 2399689 reaction equation
[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]#[N:23])=[N:14][CH:15]=2)[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=2[N:5]=1)[CH2:2][CH3:3].[N-:28]=[N+:29]=[N-:30].[Na+].C([Sn](Cl)(CCCC)CCCC)CCC>>[CH2:1]([C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:30][N:29]=[N:28][N:23]=3)=[N:14][CH:15]=2)[C:7]2[CH:24]=[CH:25][CH:26]=[CH:27][C:6]=2[N:5]=1)[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 15096Tributyltin ChlorideHCID 33557Sodium AzideHCID 19383105HCID 19383105, compound

Product 1

HCID 178439872HCID 178439872, compoundYield 51.6%

Procedure

A mixture of 2-propyl-1-[[2-(2-cyanophenyl)-5-pyridinyl]methyl]-1H-benzimidazole (0.50 g, 1.42 mmol), NaN3 (0.18 g, 2.84 mmol), and tri-n-butyltin chloride (0.92 g, 2.84 mmol) in xylenes (10 mL) was heated under reflux for 48 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 trituration with EtOH gave 0.29 g (51%) of product as a white solid, mp 240°-241° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 48 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 by flash chromatography (5% MeOH/CH2Cl2) and trituration with EtOH

Sources & evidence

ORD record
ord-93afd09932a044af8708f31d110cf6c9
Source dataset
uspto-grants-1995_09
Patent number
US05451583

Reaction notes

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