Pyridine → 2-(2-Isocyanatoethyl)bicyclo[2.2.1]heptane

Reaction equation

C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[CH:18]12[CH2:24][CH:21]([CH2:22][CH2:23]1)[CH2:20][CH:19]2[CH2:25][CH2:26]C(O)=O.[N:30]1[CH:35]=CC=CC=1>>[CH:18]12[CH2:24][CH:21]([CH2:22][CH2:23]1)[CH2:20][CH:19]2[CH2:25][CH2:26][N:30]=[C:35]=[O:8]

Participants

Reactant 3

HCID 1049Pyridine

HCID 199401P,P-Diphenylphosphinic azide

HCID 21715380HCID 21715380, compound

Product 1

HCID 205251202-(2-Isocyanatoethyl)bicyclo[2.2.1]heptane

Conditions

Temperature: 80 °C

Procedure

Diphenylphosphoryl azide (6.05 g.) was added dropwise to a solution of 3-(2-norbornyl)propionic acid (3.36 g.) in dry pyridine (20 ml.) and stirred at 80° C. for 30 minutes to give 2-(2-norbornyl)ethyl isocyanate (I.R. 2260 cm-1).

Sources & evidence

ORD record: ord-bfc531c944ca40f88b37521aa82b436a
Source dataset: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04349552

Reaction notes

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