Thionyl Chloride → HCID 20505475, compound

HRID 355245Notes

Reaction equation

[N:1]([CH:4]([CH3:10])[CH2:5][CH2:6][C:7](O)=[O:8])=[N+:2]=[N-:3].S(Cl)([Cl:13])=O>>[N:1]([CH:4]([CH3:10])[CH2:5][CH2:6][C:7]([Cl:13])=[O:8])=[N+:2]=[N-:3]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 22471948HCID 22471948, compound

Product 1

HCID 20505475HCID 20505475, compoundYield 75.1%

Procedure

A mixture of crude 4-azidopentanoic acid (8.0 g, 56 mmol) and thionyl chloride (10 g, 84 mmol) was heated at 40°-45° C. for 1.5 h, followed by evaporation of excess thionylchloride in vacuo. The residual oil was distilled to give 6.8 g (75%) of the title compound, bp 60°-65° C./0.3 mm: 1Hmr (CDCl3) δ: 3.55 (1H, q, J=13 Hz), 3.03 (2H, t, J=13 Hz), 1.9 (2H, t, J=13 Hz and 1.3 ppm (3H, d, J=13 Hz); ir (neat νmax : 2100, 1792 cm-1.

Workup

temperaturewas heated at 40°-45° C. for 1.5 h
customfollowed by evaporation of excess thionylchloride in vacuo
distillationThe residual oil was distilled

Sources & evidence

ORD record: ord-007c5c71edc94ad1a5a9aee70afd85bf
Source dataset: uspto-grants-1983_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04378314

Reaction notes

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