Pyridine → 3-Pyridinyl carbonochloridate

HRID 1421250Notes

Reaction equation

HRID 1421250 reaction equation
[C:1](Cl)([Cl:3])=[O:2].C1(C)C=CC=CC=1.[OH:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.N1C=CC=CC=1>C(Cl)Cl>[Cl:3][C:1]([O:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=[O:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 1140TolueneHCID 6371PhosgeneHCID 79713-Hydroxypyridine

Product 1

HCID 154347383-Pyridinyl carbonochloridate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1.93M solution of phosgene in toluene (20%) (198.3 ml) (382.3 mmoles) was diluted with dry CH2Cl2 (100 ml) and the mixture was stirred at 0° under an argon atmosphere. A solution of 3-hydroxy-pyridine (7.27 grams) (76.5 mmoles) and dry pyridine (8.06 grams) (8.25 ml) (101.9 mmoles) in dry CH2Cl2 (200 ml) was added dropwise to the stirred solution at 0° over a period of 1 hour. The mixture was stirred at 0-25° for an additional 2 hours. A stream of nitrogen was passed through the solution to remove most of the phosgene and the solution was then evaporated to dryness to give the title compound which was dried in vacuo for 1 hour and then taken up in dry CH2Cl2 (60 ml) and dry pyridine (60 ml) to give a stock solution of the title compound.

Workup

  1. stirringThe mixture was stirred at 0-25° for an additional 2 hours
  2. customto remove most of the phosgene
  3. customthe solution was then evaporated to dryness

Sources & evidence

ORD record
ord-6b7ad124bbec44739ffb5db9f674bc7e
Source dataset
uspto-grants-2000_06
Patent number
US06075025

Reaction notes

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