Chloride → HCID 67313482, compound

HRID 1391499Notes

Reaction equation

HRID 1391499 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](Cl)=[N:10][OH:11].[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]#[C:21][C:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:23].C(=O)(O)[O-].[Na+].[Cl-]>C(O)(C)C.CCOCC>[Cl:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[O:11][N:10]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[C:21]=1[C:22]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)=[O:23]

Participants

7

Reactant 4

HCID 312ChlorideHCID 516892Sodium Bicarbonate2×HCID 2799903HCID 2799903, compoundHCID 67313799HCID 67313799, compound

Product 1

HCID 67313482HCID 67313482, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 56 mg (0.25 mmol) of 2,4-dichloro-N-hydroxybenzenecarboximidoyl chloride, 60 mg (0.25 mmol) of 3-(2-chlorophenyl)-1-(3-pyridyl)-2-propyn-1-one, and 30 mg (0.36 mmol) of sodium bicarbonate in 2.5 mL of isopropyl alcohol was heated at 55° C. overnight with shaking. An additional 30 mg of carboximidoyl chloride and 15 mg of sodium bicarbonate was then added, and the mixture was heated for another 20 hrs. The reaction mixture was cooled, diluted with ether, and then washed with saturated sodium bicarbonate. The ether fraction was dried over magnesium sulfate. The drying agent was filtered off, and the ether was removed by rotoevaporation. The crude product was purified by prep TLC to give 90 mg (0.21 mmol) of 5-(2-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)carbonyl]isoxazole. 1H NMR (CDCl3): δ 7.16 (m, 1), 7.60 (m,2), 7.92 (m, 1), 8.53 (br d, 1), and 8.74 ppm (br s, 1). MS m/z: 428.9 (M+H).

Workup

  1. temperaturethe mixture was heated for another 20 hrs
  2. temperatureThe reaction mixture was cooled
  3. washwashed with saturated sodium bicarbonate
  4. dry with materialThe ether fraction was dried over magnesium sulfate
  5. filtrationThe drying agent was filtered off
  6. customthe ether was removed by rotoevaporation
  7. customThe crude product was purified by prep TLC

Sources & evidence

ORD record
ord-09ef2f048b974ae191c4136b17f9317b
Source dataset
uspto-grants-2008_03
Patent number
US07338967B2

Reaction notes

Loading…