Thionyl Chloride → Azido-PEG1-CH2COO-Cl
Reaction equation
[N:1]([CH2:4][CH2:5][O:6][CH2:7][C:8]([OH:10])=O)=[N+:2]=[N-:3].S(Cl)([Cl:13])=O>>[N:1]([CH2:4][CH2:5][O:6][CH2:7][C:8]([Cl:13])=[O:10])=[N+:2]=[N-:3]Participants
3
Procedure
A solution of 2-azidoethoxyacetic acid (2.09 g, 14.4 mmol) in thionyl chloride (5 ml) was stirred at room temperature for 4 h. The excess thionyl chloride was removed under the vacuum of the water aspirator and the residue dissolved in benzene (10 ml, dried over molecular sieves) was evaporated in vacuo. The oil so obtained was dried in vacuo (water pump) over NaOH for 1 h yielding 2.23 g (13.6 mmol, 94.4%) of 2-azidoethoxyacetyl chloride as a colourless oil: 1Hmr (CDCl3) δ: 3.43 (2H, br. t, J=5 Hz, --CH2O--) 3.78 (2H, br. t, J=5 Hz, --CH2N3) and 4.50 ppm (2H, s, --COCH2O--); ir (neat) νmax : 2100 (azide) and 1800 cm-1 (--COCl). This material was used in the next reaction without any purification.
Workup
- customThe excess thionyl chloride was removed under the vacuum of the water aspirator
- dissolutionthe residue dissolved in benzene (10 ml, dried over molecular sieves)
- customwas evaporated in vacuo
- customThe oil so obtained
- dry with materialwas dried in vacuo (water pump) over NaOH for 1 h
Sources & evidence
- ORD record
- ord-fafb31963c354168acda5d8db9dba5a0
- Source dataset
- uspto-grants-1984_07
- Patent number
- US04461727
Reaction notes
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