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

Reactant 2

HCID 24386Thionyl Chloride

HCID 111161715-azidopentanoic Acid

Product 1

HCID 109317475-azidopentanoyl Chloride

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-fe53156053ef408e8a9cfeb9bc250fdc
Source dataset: uspto-grants-1981_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04272437

Reaction notes

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