Triethylamine → N-{4-[3,5-bis(Trifluoromethyl)pyrazol-1-yl]phenyl}-2-methylbenzamide

HRID 1634083Notes

Reaction equation

HRID 1634083 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17]([F:20])([F:19])[F:18])=[N:9]2)=[CH:4][CH:3]=1.[C:21]1([CH3:30])[C:22]([C:27](Cl)=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=1.C(N(CC)CC)C>C(Cl)Cl>[F:18][C:17]([F:20])([F:19])[C:10]1[CH:11]=[C:12]([C:13]([F:14])([F:15])[F:16])[N:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:27](=[O:28])[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[CH3:30])=[CH:7][CH:6]=2)[N:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 27406684-(3,5-Bis(trifluoromethyl)-1H-pyrazol-1-yl)aniline

Product 1

HCID 10158634N-{4-[3,5-bis(Trifluoromethyl)pyrazol-1-yl]phenyl}-2-methylbenzamideYield 46.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1-(4′-aminophenyl)-3,5-bis(trifluoromethyl)pyrazole (0.10 g, 0.34 mmol), o-toluoyl chloride (0.062 mL, 0.43 mmol), and triethylamine (0.06 mL, 0.43 mmol) in methylene chloride (7 mL) was stirred under argon for three days. The reaction mixture was diluted with methylene chloride, washed with 1N hydrochloric acid (2×50 mL), brine (2×40 mL), dried (magnesium sulfate) and concentrated to give an off-white solid. Recrystallization from methylene chloride/hexanes gave the above-named compound (0.065 g). m.p. 175° C. NMR (CDCl3, 400 MHz): δ 7.83 (d, 2H), 7.64 (br s, 1H), 7.53 (m, 3H), 7.43 (m, 1H), 7.31 (m, 2H), 7.10 (s, 1H), 2.56 (s, 3H).

Workup

  1. washwashed with 1N hydrochloric acid (2×50 mL), brine (2×40 mL)
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated
  4. customto give an off-white solid
  5. customRecrystallization from methylene chloride/hexanes

Sources & evidence

ORD record
ord-347ce40611574b4f94fad05aab26ef1e
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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