Reaction #2175448

ord-f3a9432c4ea54444b74230184f7ae793

Reaction equation

[N-]=[N+]=[N-].[Na+]
Sodium azide
Cc1ccc(S(=O)(=O)OCCOCCOCCOCCOS(=O)(=O)c2ccc(C)cc2)cc1
tetraethylene glycol ditosylate
→
Cc1ccc(S(=O)(=O)OCCOCCOCCOCCN=[N+]=[N-])cc1
8
Yield 19.0%
Cc1ccc(S(=O)(=O)OCCOCCOCCOCCN=[N+]=[N-])cc1
11-azido-3,6,9-trioxa-undecanyl p-toluenesulfonate
Yield 19.0%

Reactants

[N-]=[N+]=[N-].[Na+]
Sodium azide
Cc1ccc(S(=O)(=O)OCCOCCOCCOCCOS(=O)(=O)c2ccc(C)cc2)cc1
tetraethylene glycol ditosylate

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Sodium azide and tetraethylene glycol ditosylate were reacted according Example 7 p to yield 0.7 g (19%) of 8 as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 2.44 (s, 3H), 3.38 (t, J=5.2 Hz, 2H), 3.55-3.70 (m, 12H), 4.16 (t, J=5.2 Hz, 2H), 7.34 (d, J=8.4 Hz, 2H), 7.78 (d, J=8.4 Hz, 2H); 13C NMR (100.6 MHz, CDCl3): δ 21.6, 50.7, 68.7, 68.8, 69.2, 70.0, 70.6-70.7, 127.9, 129.8, 133.1, 144.7 MS ESI (m/z): [M+H]+ calcd. for C15H24O6N3S, 374.2; found 374.2

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08435488B2uspto-grants-2013_05