Thionyl Chloride → 5-azidopentanoyl Chloride
Reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=O)=[N+:2]=[N-:3].S(Cl)([Cl:13])=O>>[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][C:8]([Cl:13])=[O:10])=[N+:2]=[N-:3]Participants
3
Conditions
- Temperature
- 60 °C
Procedure
In a one neck round bottom flask containing 5-azidopentanoic acid (0.88 g, 0.068 mol) was added thionyl chloride (7.35 ml, 0.102 mol). The reaction mixture was stirred at 60° C. for 2 h and the thionyl chloride was evaporated under reduced pressure to give crude 5-azidopentanoyl chloride. The distillation of crude acyl chloride gave a colorless liquid; 6.93 (62%), bp 111°-4° C. (1.2-1.4 mm); ir (neat) νmax : 2100 (N3) and 1800 cm-1 (C=O); 1Hmr (CDCl3) δ: 3.37 (2H,δ-H), 3.00 (2H, α-H) and 2.1-1.2 ppm (4H, β-H and γ-H).
Workup
- customthe thionyl chloride was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-b2fb749676a3449195879a5eb10e37d1
- Source dataset
- uspto-grants-1983_03
- Patent number
- US04378314
Reaction notes
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