Triethylamine → N,N-dimethyl-2-(3-trifluoromethylbenzoyl) nicotinamide

HRID 275261Notes

Reaction equation

HRID 275261 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[C:6]([C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](Cl)=[O:11])=[O:7].Cl.[CH3:23][NH:24][CH3:25].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:23][N:24]([CH3:25])[C:10](=[O:11])[C:9]1[CH:13]=[CH:14][CH:15]=[N:16][C:8]=1[C:6](=[O:7])[C:5]1[CH:17]=[CH:18][CH:19]=[C:3]([C:2]([F:21])([F:20])[F:1])[CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 200876762-(3-Trifluoromethylbenzoyl)nicotinoyl chloride

Product 1

HCID 20087671N,N-dimethyl-2-(3-trifluoromethylbenzoyl) nicotinamide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from step (i) above was dissolved in dry toluene (10 ml). Dimethylamine hydrochloride (1.3 g) was added followed by triethylamine (1.94 g). The mixture was then stirred at room temperature for 4.5 hours. The mixture was diluted with ethyl acetate and washed successively with ethyl acetate and washed successively with 2N sodium carbonate, 2N hydrochloric acid then water. The organic phase was dried then evaporated to yield a red-brown gum which was triturated in hexane to yield the title product as a beige solid (0.64 g), m.p.100°-103° C.

Workup

  1. washwashed successively with ethyl acetate
  2. washwashed successively with 2N sodium carbonate, 2N hydrochloric acid
  3. customThe organic phase was dried
  4. customthen evaporated
  5. customto yield a red-brown gum which
  6. customwas triturated in hexane

Sources & evidence

ORD record
ord-71b361b3751340398fd8c6ee48cbe87b
Source dataset
uspto-grants-1995_02
Patent number
US05393730

Reaction notes

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