Water → Tributyltin azide

HRID 1975058Notes

Reaction equation

HRID 1975058 reaction equation
O.[N-:2]=[N+:3]=[N-:4].[Na+].[CH2:6]([Sn:10](Cl)([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH3:9]>COC(C)(C)C>[CH2:15]([Sn:10]([N:2]=[N+:3]=[N-:4])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:11][CH2:12][CH2:13][CH3:14])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 15096Tributyltin Chloride2×HCID 33557Sodium Azide

Product 1

HCID 4984872Tributyltin azideYield 65%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Into 40 ml of distilled water was added 9.99 g of sodium azide (0.154 mol, 10.0 equiv), 30 ml tert-butyl methyl ether, and 5.0 g (0.0154 mol, 1.0 equiv) tributyltin chloride. The resultant mixture was stirred at room temperature for one hour. Carbon 13 NMR of an aliquot taken at this point showed absence of the starting tributyltin chloride. Therefore, the organic layer, after being separated from the aqueous layer, was dried over anhydrous sodium sulfate, filtered, concentrated, and distilled to afford 3.29 g (65%) of the desired product (bp.=115°-117° C./0.4 mm): 13C NMR δ27.8, 27.0, 15.2, 13.6.

Workup

  1. customTherefore, the organic layer, after being separated from the aqueous layer
  2. dry with materialwas dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-030d3580b6914027b0e9f07c5a3a0234
Source dataset
uspto-grants-1994_02
Patent number
US05284841

Reaction notes

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