Triethylamine → HCID 9861484, compound

HRID 567670Notes

Reaction equation

HRID 567670 reaction equation
[NH2:1][C:2]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([Cl:12])[C:3]=1[C:4]([OH:6])=[O:5].C(N(CC)CC)C.[F:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=O>CCCCCCC.C(OCC)(=O)C>[Cl:12][C:7]1[C:3]2[C:4](=[O:6])[O:5][C:23]([C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[F:20])=[N:1][C:2]=2[C:10]([Cl:11])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 98082-Fluorobenzoyl chlorideHCID 6045422-Amino-3,6-dichlorobenzoic acid

Product 1

HCID 9861484HCID 9861484, compound

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

2-Amino-3,6-dichlorobenzoic acid (0.5 g) and triethyl amine (20 ml) were mixed. 2-Fluorobenzoyl chloride (0.77 g) was added dropwise under cooling and stirring. The mixture was subsequently heated to RT and stirred until disappearance of starting material was seen on TLC (silicagel) using heptane/ethyl acetate (4/1) as eluent. After cooling on ice the precipitate was filtered off and the filtrate evaporated to dryness. The residue was partitioned between methylene chloride and potassium carbonate (2N), the organic layers separated, dried over magnesium sulfate and evaporated to dryness. The raw product was purified by column chromatography on silicagel using heptane/ethyl acetate as eluent. Yield 0.31 g. m.p. 140° C.

Workup

  1. temperatureunder cooling
  2. stirringstirred until disappearance of starting material
  3. temperatureAfter cooling on ice the precipitate
  4. filtrationwas filtered off
  5. customthe filtrate evaporated to dryness
  6. customThe residue was partitioned between methylene chloride and potassium carbonate (2N)
  7. customthe organic layers separated
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness
  10. customThe raw product was purified by column chromatography on silicagel

Sources & evidence

ORD record
ord-99e52a8203e14f49a27bf165a2bcb35f
Source dataset
uspto-grants-2001_01
Patent number
US06180625B2

Reaction notes

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