Pyridine → (5-Cyanopyridin-2-yl)(methyl)carbamic chloride

HRID 539582Notes

Reaction equation

HRID 539582 reaction equation
C(=O)(OC(Cl)(Cl)Cl)[O:2][C:3]([Cl:6])(Cl)Cl.N1C=CC=CC=1.[CH3:19][NH:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][N:22]=1>O1CCCC1>[C:25]([C:24]1[CH:27]=[CH:28][C:21]([N:20]([CH3:19])[C:3]([Cl:6])=[O:2])=[N:22][CH:23]=1)#[N:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 178608996-(Methylamino)pyridine-3-carbonitrile

Product 1

HCID 86720259(5-Cyanopyridin-2-yl)(methyl)carbamic chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of bis(trichloromethyl) carbonate (50 mg, 0.17 mmol) in tetrahydrofuran (2.0 mL) was added pyridine (0.04 mL, 0.510 mmol) dropwise under ice-cooling. After stirring under ice-cooling for 30 min, 6-(methylamino)nicotinonitrile (68 mg, 0.510 mmol) was added and the mixture was stirred at room temperature for 2.5 hours. The precipitated solid was filtered off. The filtrate containing (5-cyanopyridin-2-yl)(methyl)carbamic chloride (I-28) was directly used for next step.

Workup

  1. temperaturecooling
  2. temperaturecooling for 30 min
  3. stirringthe mixture was stirred at room temperature for 2.5 hours
  4. filtrationThe precipitated solid was filtered off
  5. additionThe filtrate containing (5-cyanopyridin-2-yl)(methyl)carbamic chloride (I-28)

Sources & evidence

ORD record
ord-dae7440a6e7a4fee95adafc6f1c6a2f1
Source dataset
uspto-grants-2014_10
Patent number
US08871754B2

Reaction notes

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