Triethylamine → N-(5-(trifluoromethyl)pyridin-2-yl)pivalamide

HRID 1948625Notes

Reaction equation

HRID 1948625 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([NH2:9])=[N:7][CH:8]=1.CCN(CC)CC.[CH3:19][C:20]([CH3:25])([CH3:24])[C:21](Cl)=[O:22]>C(Cl)Cl>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:21](=[O:22])[C:20]([CH3:25])([CH3:24])[CH3:19])=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 7358622-Amino-5-(trifluoromethyl)pyridine

Product 1

HCID 58563823N-(5-(trifluoromethyl)pyridin-2-yl)pivalamideYield 91.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

5-(trifluoromethyl)pyridin-2-amine (15 g, 92.5 mmole) was taken up in DCM (190 ml) under nitrogen and NEt3 (16 ml, 115.7 mmole) was added. The solution was cooled to −5° C., a solution of trimethyl acetyl chloride (12.5 ml, 101.8 mmole) in DCM (65 ml) was added dropwise, and the mixture was stirred for a further 15 minutes in an ice bath. The mixture was then stirred for 2 hours at RT. The suspension was washed with H2O (150 ml), then with dilute NaHCO3 solution, and the organic phase was dried over MgSO4. After filtering off the drying agent and removing the solvent on a rotary evaporator the residue was crystallised. N-(5-(trifluoromethyl)pyridin-2-yl)pivalamide (20.8 g, 91) was obtained.

Workup

  1. stirringThe mixture was then stirred for 2 hours at RT
  2. washThe suspension was washed with H2O (150 ml)
  3. dry with materialwith dilute NaHCO3 solution, and the organic phase was dried over MgSO4
  4. filtrationAfter filtering off the drying agent
  5. customremoving the solvent
  6. customon a rotary evaporator the residue
  7. customwas crystallised

Sources & evidence

ORD record
ord-e342df3dcce6419bb1f50e81890e765e
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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