Sodium Azide → Azido(trioctyl)stannane

HRID 1831015Notes

Reaction equation

HRID 1831015 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([Sn:13](Cl)([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]>O>[CH2:22]([Sn:13]([N:1]=[N+:2]=[N-:3])([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 75757Trioctyltin chloride

Product 1

HCID 71354122Azido(trioctyl)stannane

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
6.5 °C

Procedure

Sodium azide (160 kg) was dissolved in pure water (505 L), and the solution was cooled to 3 to 10° C. Trioctyltin chloride [TOTC] (847 kg) was added dropwise over 1 to 3 hours, followed by stirring at 5 to 10° C. for about 2 hours. The reaction solution was extracted with methylene chloride (1822 kg, then 546 kg). The methylene chloride layer was washed with a mixture of pure water (50 L) and a 10% aqueous sodium chloride solution (440 L), and the methylene chloride layer was concentrated under reduced pressure to give trioctyltin azide [TOTA].

Workup

  1. extractionThe reaction solution was extracted with methylene chloride (1822 kg
  2. washThe methylene chloride layer was washed with a mixture of pure water (50 L)
  3. concentrationa 10% aqueous sodium chloride solution (440 L), and the methylene chloride layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-675d9783d188489daea6209980e3b7a1
Source dataset
uspto-grants-2006_06
Patent number
US07067546B2

Reaction notes

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