Sodium Azide → 3-(Trioctylstannyl)triaza-1,2-dien-2-ium-1-ide

HRID 567401Notes

Reaction equation

HRID 567401 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 713541223-(Trioctylstannyl)triaza-1,2-dien-2-ium-1-ide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
6.5 °C

Procedure

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

Workup

  1. extractionThe reaction solution was extracted with methylene chloride (1822 kg, followed by 546 kg)
  2. washThe methylene chloride layer was washed with a mixture of deionized water (50 L) and 10% sodium chloride solution (440 L)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9c7b964c91ef4f88905d617fe6a1cff3
Source dataset
uspto-grants-2001_01
Patent number
US06177587B1

Reaction notes

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