Sodium Azide → HCID 14625416, compound

HRID 1638894Notes

Reaction equation

HRID 1638894 reaction equation
[NH2:1][S:2]([C:5]1[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=1[C:7]([O:9][CH2:10][CH2:11]I)=[O:8])(=[O:4])=[O:3].[N-:17]=[N+:18]=[N-:19].[Na+]>C(O)C>[NH2:1][S:2]([C:5]1[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=1[C:7]([O:9][CH2:10][CH2:11][N:17]=[N+:18]=[N-:19])=[O:8])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 33557Sodium Azide2×HCID 14625415HCID 14625415, compound

Product 1

HCID 14625416HCID 14625416, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.6 g of the product from Example 2 and 0.3 g of sodium azide in 10 mL absolute ethanol was heated at reflux temperature for 24 hours. Additional sodium azide (0.3 g) was added and the suspension was heated for another 24 hours. The reaction mixture was cooled to room temperature and the ethanol was removed in vacuo. The resultant crude oil was purified by careful chromatography on silica gel. Elution with 1:1 hexane/ethyl acetate gave 0.5 g of the desired product as a colorless, viscous oil; IR (film): 1720, 2100 cm-1 ; NMR (CDCl3): δ 3.67 (t, 2H, J=4 Hz), 4.55 (t, 2H, J=4 Hz), 5.77 (br s, 2H), 7.65 (m, 2H), 7.9 (m, 1H), 8.15 (m, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 24 hours
  3. temperaturethe suspension was heated for another 24 hours
  4. customthe ethanol was removed in vacuo
  5. customThe resultant crude oil was purified by careful chromatography on silica gel
  6. washElution with 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-b52d284a4bdd496ca3a6d7ba79dd88ae
Source dataset
uspto-grants-1989_11
Patent number
US04881968

Reaction notes

Loading…