Triethylamine → HCID 3362587, compound

HRID 2084261Notes

Reaction equation

HRID 2084261 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[F:11][C:12]([F:23])([F:22])[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[CH:16]=[N:17][NH2:18].CCN(CC)CC>C1COCC1>[F:11][C:12]([F:22])([F:23])[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[CH:16]=[N:17][NH:18][C:4]([C:3]1[C:2]([Cl:1])=[N:10][CH:9]=[CH:8][CH:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27745412-Chloronicotinoyl chlorideHCID 69356013HCID 69356013, compound

Product 1

HCID 3362587HCID 3362587, compoundYield 110.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-chloro-nicotinoyl chloride (1.75 g, 10 mmol) in 40 mL THF was added 3-trifluoromethyl-benzylidene-hydrazine (1.88 g, 10 mmol) in 20 mL THF at 0° C., followed by 1.5 mL Et3N. The solution was stirred at room temperature overnight and precipitate was observed. It was filtered and the solid was washed with MeOH, dried to yield the title compound (3.63 g, 90%). 1H NMR (acetone-d6): 11.08 (s, 1H), 8.53 (d, J=4.5 Hz, 2H), 8.27 (s, 1H), 7.72 (m, 3H), 7.57 (m, 2H).

Workup

  1. filtrationIt was filtered
  2. washthe solid was washed with MeOH
  3. customdried

Sources & evidence

ORD record
ord-705f4babb8294a8cb324f98de0f32f4f
Source dataset
uspto-grants-2004_04
Patent number
US06716859B2

Reaction notes

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