Dichloroacetyl chloride → HCID 3007230, compound

HRID 2053386Notes

Reaction equation

HRID 2053386 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:12]=[C:11]([C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:20])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[Cl:28][CH:29]([Cl:33])[C:30](Cl)=[O:31]>O1CCCC1>[Cl:28][CH:29]([Cl:33])[C:30]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]2[CH:12]=[C:11]([C:13]3[C:14]([Cl:20])=[CH:15][CH:16]=[CH:17][C:18]=3[Cl:19])[O:10][N:9]=2)[CH:3]=1)=[O:31]

Participants

5

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 8471TriethylamineHCID 21100343HCID 21100343, compound

Product 1

HCID 3007230HCID 3007230, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(3-Aminophenyl)-5-(2,6-dichlorophenyl)isoxazole (60 mg, 0.2 mmol) was dissolved in anhydrous tetrahydrofuran (10 mL) with triethylamine (33 mL, 0.24 mmol). The mixture was cooled in an ice-bath under nitrogen, then a solution of dichloroacetyl chloride (23 mL, 0.24 mmol) in anhydrous tetrahydrofuran (5 mL) was added dropwise. After the addition was completed the ice-bath was removed and the mixture was stirred at room temperature for 12 h. The solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate and washed successively with water and brine. The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting solid was purified by column chromatography on silica gel, eluting with 8:2 hexanes-ethyl acetate. The appropriate fractions were combined to give the title compound as a tan solid, 74 mg.

Workup

  1. temperatureThe mixture was cooled in an ice-bath under nitrogen
  2. additionAfter the addition
  3. customwas removed
  4. customThe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed successively with water and brine
  7. dry with materialThe ethyl acetate solution was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting solid was purified by column chromatography on silica gel
  11. washeluting with 8:2 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-75e71b20ff534386b3298802d2571d43
Source dataset
uspto-grants-2008_02
Patent number
US07326790B2

Reaction notes

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