Triethylamine → 2-chloro-5-isocyanatopyridine

HRID 2102744Notes

Reaction equation

HRID 2102744 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5](C(O)=O)=[CH:4][N:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:18])C=CC=CC=1.C([N:30]([CH2:33]C)CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([N:30]=[C:33]=[O:18])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 792226-Chloronicotinic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 49612732-chloro-5-isocyanatopyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a suspension of 6-chloro-nicotinic acid (0.468 g, 3 mmol) (Aldrich) in toluene (15 mL) was added diphenylphosphoryl azide (0.958 g, 3.5 mmol) (Aldrich), followed by the addition of triethylamine (0.35 g, 3.6 mmol) (Aldrich). The mixture was stirred at room temperature for 30 minutes and the mixture became clear. Then the mixture was heated at 80° C. for 2 hours. The mixture was cooling down to room temperature to give crude 2-chloro-5-Isocyanato-pyridine as 0.2 M solution of toluene and used for the next step without further purification.

Workup

  1. temperatureThen the mixture was heated at 80° C. for 2 hours
  2. temperatureThe mixture was cooling down to room temperature

Sources & evidence

ORD record
ord-c1789dabdb66425580facd303df5ee44
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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