Thionyl Chloride → 3-Azido-3-methylbutanoyl chloride
Reaction equation
[N:1]([C:4]([CH3:10])([CH3:9])[CH2:5][C:6](O)=[O:7])=[N+:2]=[N-:3].S(Cl)([Cl:13])=O>ClC(Cl)C>[N:1]([C:4]([CH3:10])([CH3:9])[CH2:5][C:6]([Cl:13])=[O:7])=[N+:2]=[N-:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a stirred solution of 3-azido-3-methylbutanoic acid (10 g, 69.8 mmol) in anh. dichloroethane (50 mL) was added thionyl chloride in one portion (10.0 mL, 2 equiv, 0.14 mol). The flask was fitted with a condenser and the reaction was heated in a 50° C. oil bath for 2 h. The reaction was concentrated to a brown-black suspension. The residue was vacuum distilled through a short path distillation apparatus. The forerun was discarded and the major fraction distilled at 66° C. at 18 mbar as a pale yellow liquid (9.66 g, 85.6%). 1H NMR (CDCl3, 400 MHz): δ 1.41 (s, 6H), 2.51 (s, 2H), 2.98 (s, 2 H).
Workup
- customThe flask was fitted with a condenser
- concentrationThe reaction was concentrated to a brown-black suspension
- distillationdistilled through a short path distillation apparatus
- distillationthe major fraction distilled at 66° C. at 18 mbar as a pale yellow liquid (9.66 g, 85.6%)
Sources & evidence
- ORD record
- ord-dcd5c900f79d4c128d5943eca707d46e
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278482B2
Reaction notes
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