Stannous Chloride → HCID 19710468, compound

HRID 726164Notes

Reaction equation

HRID 726164 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-])=O)([O-])=O.Cl[Sn]Cl>Cl>[NH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][NH:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH2:1]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 19710464HCID 19710464, compound

Product 1

HCID 19710468HCID 19710468, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

26.1 g N,N'-bis(2-nitrophenyl)-1,8-diamino-3,6-dioxaoctane is dissolved in 100 ml concentrated HCl and stirred while 92.5 g SnCl2 dissolved in 100 ml concentrated HCl are added during approximately two minutes. The reaction is exothermal and the temperature rises to 90° C. at the same time as the colour changes from light orange through dark to light green, whereafter a product starts to precipitate. After one hour the reaction mixture is cooled on an ice bath. The crystalline product is filtered off and dissolved in 150 ml water and added to 50 g NaOH in 300 ml ice water. A greenish oil is separated. The product is extracted with 100+50 ml CH2Cl2, dried over MgSO4, and evaporated under vacuum. Yield: 21.7 g (57.9 mmol, N,N'-bis(2-aminophenyl)-1,8-diamino-3,6-dioxaoctane.

Workup

  1. additionare added during approximately two minutes
  2. customrises to 90° C. at the same time as the colour changes from light
  3. customto precipitate
  4. temperatureAfter one hour the reaction mixture is cooled on an ice bath
  5. filtrationThe crystalline product is filtered off
  6. dissolutiondissolved in 150 ml water
  7. additionadded to 50 g NaOH in 300 ml ice water
  8. customA greenish oil is separated
  9. extractionThe product is extracted with 100+50 ml CH2Cl2
  10. dry with materialdried over MgSO4
  11. customevaporated under vacuum

Sources & evidence

ORD record
ord-b6e944c1eb6445879fbf226903d01962
Source dataset
uspto-grants-1998_01
Patent number
US05708123

Reaction notes

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