5-Chlorosalicylic Acid → HCID 24872053, compound

HRID 2241919Notes

Reaction equation

HRID 2241919 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[F:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[NH2:16].P(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([NH:16][C:15]1[CH:17]=[CH:18][C:19]([N:20]2[CH2:21][CH2:22][O:23][CH2:24][CH2:25]2)=[C:13]([F:12])[CH:14]=1)=[O:9]

Participants

5

Reactant 3

HCID 94475-Chlorosalicylic AcidHCID 24387Phosphorus trichlorideHCID 14853303-Fluoro-4-morpholinoaniline

Product 1

HCID 24872053HCID 24872053, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-chlorosalicylic acid (0.30 g, 1.738 mmol), 3-fluoro-4-morpholinoaniline (compound of Reference Example 74; 0.34 g, 1.738 mmol), phosphorus trichloride (0.08 ml, 0.869 mmol) and toluene (6 ml) was refluxed for 1.5 hours. The reaction mixture was cooled to the room temperature, and extracted with ethyl acetate after addition of water. The ethyl acetate layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was washed with diisopropyl ether to give the title compound (0.30 g, 49%) as a colorless crystal.

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. extractionextracted with ethyl acetate
  3. additionafter addition of water
  4. washThe ethyl acetate layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe residue obtained by evaporation of the solvent under reduced pressure
  7. washwas washed with diisopropyl ether

Sources & evidence

ORD record
ord-d5f3a8b47fda44129cf11346f10db5f2
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

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