Triethylamine → HCID 3349692, compound

HRID 1859665Notes

Reaction equation

HRID 1859665 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5](Cl)=[O:6].[F:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21].C(N(CC)CC)C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[Cl:11])[C:5]([NH:17][C:16]1[CH:18]=[CH:19][C:13]([F:12])=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=1)=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 677684-Fluoro-3-nitroanilineHCID 76403Benzoyl chloride, 3,4-dichloro-

Product 1

HCID 3349692HCID 3349692, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

3,4-Dichlorobenzoyl chloride (4.3 g, 20.5 mmol) was added all at once to 4-fluoro-3-nitroaniline (3.14 g, 20.1 mmol) and triethylamine (3 mL, 21.5 mmol) in ethyl acetate (200 mL) at room temperature. The reaction mixture was stirred overnight at room temperature then diluted to ˜500 mL with ethyl acetate. The ethyl acetate was washed successively with 1N HCl (100 mL), saturated sodium bicarbonate (100 mL), and brine (100 mL), then dried (magnesium sulfate), filtered, and stripped of solvent under reduced pressure. Trituration of the residue in hexanes (125 mL) and a few milliliters of ethyl acetate afforded the product by filtration (5.6 g); m.p. 202-204° C.

Workup

  1. washThe ethyl acetate was washed successively with 1N HCl (100 mL), saturated sodium bicarbonate (100 mL), and brine (100 mL)
  2. dry with materialdried (magnesium sulfate)
  3. filtrationfiltered
  4. customTrituration of the residue in hexanes (125 mL) and a few milliliters of ethyl acetate afforded the product
  5. filtrationby filtration (5.6 g)

Sources & evidence

ORD record
ord-131f68c5872b40a2b0c4204a26332588
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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