Thionyl Chloride → 3-Azido-3-methylbutanoyl chloride

HRID 1770702Notes

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>ClCCCl>[N:1]([C:4]([CH3:10])([CH3:9])[CH2:5][C:6]([Cl:13])=[O:7])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 3-azido-3-methylbutanoic acid (10 g, 69.8 mmol) in anhydrous 1,2-dichloroethane (50 mL) was added thionyl chloride (10.0 mL, 140 mmol). The flask was fitted with a condenser and the reaction was heated in a 50° C. oil bath for 2 hours. The reaction was concentrated to a brownish-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, 59.7 mmol, 85.6%). 1H NMR (CDCl3, 400 MHz): δ 1.41 (s, 6H), 2.51 (s, 2H), 2.98 (s, 2H). 1H NMR (CDCl3, 400 MHz): δ 1.44 (s, 6H), 3.10 (s, 2H).

Workup

customThe flask was fitted with a condenser
concentrationThe reaction was concentrated to a brownish-black suspension
distillationdistilled through a short path distillation apparatus

Sources & evidence

ORD record: ord-26d6ecac9cf24465811b2c66ac545795
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09248117B2

Reaction notes

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