Sodium Bicarbonate → HCID 11647674, compound

HRID 1672412Notes

Reaction equation

HRID 1672412 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].[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([OH:29])[C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[CH:14]=1.C(=O)(O)[O-].[Na+]>C(O)(C)C.CCOCC>[Cl:28][C:24]1[CH:23]=[C:22]([C:21]2[O:11][N:10]=[C:9]([C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[C:20]=2[CH:19]([C:15]2[CH:14]=[N:13][CH:18]=[CH:17][CH:16]=2)[OH:29])[CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 2799903HCID 2799903, compound2×HCID 67313957HCID 67313957, compound

Product 1

HCID 11647674HCID 11647674, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 53 mg (0.24 mmol) of 2,4-dichloro-N-hydroxybenzenecarboximidoyl chloride, 50 mg (0.21 mmol) of 1-(3-pyridyl)-3-(3-chlorophenyl)-2-propyn-1-ol, and 26 mg (0.31 mmol) of sodium bicarbonate in 2.5 mL of isopropyl alcohol was heated at 55° C. on a rotary table shaker equipped with a heated sand bath. After 20 hrs, an additional 20 mg of 2,4-dichloro-N-hydroxybenzenecarboximidoyl chloride and 10 mg of sodium bicarbonate was added, and the reaction mixture was stirred and heated for another 16 hrs. The mixture was then diluted with ether, and the solution was washed with saturated sodium chloride and 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 15 mg (0.035 mmol) of 5-(3-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)hydroxymethyl]isoxazole. 1H NMR (CDCl3): δ 5.92 (br s, 1), 7.04 (d of d, 1), 7.12 (d, 1), 7.72 (m, 1), 8.86 (br s, 1), and 8.29 ppm (br s, 2). MS m/z: 430.9 (M+H).

Workup

  1. customequipped with a heated sand bath
  2. temperatureheated for another 16 hrs
  3. washthe solution was washed with saturated sodium chloride
  4. dry with materialdried 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-bd7095fd8a804b6db70b3cc07125f340
Source dataset
uspto-grants-2011_08
Patent number
US07998983B2

Reaction notes

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