Methyl chloroformate → Methyl [6-(trifluoromethyl)pyridin-3-yl]carbamate

HRID 1593380Notes

Reaction equation

HRID 1593380 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[N:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.Cl[C:13]([O:15][CH3:16])=[O:14].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[F:11][C:2]([F:1])([F:10])[C:3]1[N:8]=[CH:7][C:6]([NH:9][C:13](=[O:14])[O:15][CH3:16])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 27377445-Amino-2-(trifluoromethyl)pyridine

Product 1

HCID 23082060Methyl [6-(trifluoromethyl)pyridin-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Into 15 ml of pyridine was dissolved 3.00 g of 6-(trifluoromethyl)pyridin-3-amine, and then 2.1 ml of methyl chloroformate was added thereto under ice-cooling, followed by 2 hours of stirring at room temperature. Under ice-cooling, 30 ml of a saturated sodium bicarbonate aqueous solution was added to the reaction solution, followed by 1 hour of stirring. Thereafter, the precipitated crystals were filtrated and, after washing with water, dried under reduced pressure to obtain 3.88 g of the title compound.

Workup

  1. temperatureunder ice-cooling
  2. temperatureUnder ice-cooling
  3. waitfollowed by 1 hour
  4. stirringof stirring
  5. filtrationThereafter, the precipitated crystals were filtrated
  6. washafter washing with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-5559a5419f414fab9b82dd2c322ea1b0
Source dataset
uspto-grants-2007_11
Patent number
US07297698B2

Reaction notes

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