Potassium Carbonate → HCID 18949260, compound

HRID 1768673Notes

Reaction equation

HRID 1768673 reaction equation
[CH3:1][C:2]([CH3:15])([CH3:14])[C:3]([C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][CH:6]=1)=O.Cl.[CH3:17][O:18][NH2:19].C(=O)([O-])[O-:21].[K+].[K+]>O1CCCC1>[CH3:1][C:2]([CH3:15])([CH:14]=[O:21])[CH2:3][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:19][O:18][CH3:17])=[O:10])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 11806342Benzoyl chloride, 4-(2,2-dimethyl-1-oxopropyl)-

Product 1

HCID 18949260HCID 18949260, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
23 °C

Procedure

A solution of 67.2 grams of 4-(2,2-dimethyl-1-oxopropyl)-benzoyl chloride dissovled in 100 millimeters of tetrahydrofuran (THF) is added dropwise to a suspension of 25.0 grams of methoxyamine hydrochloride and 256 grams of finely ground anhydrous potassium carbonate in 1.1 liters of THF. The reaction mixture is stirred at 23° C. overnight and then heated to 50° to 55° C. for 5 hours. This mixture is cooled to room temperature and filtered. The residue is washed with THF, and the filtrates are combined and evaporated to dryness. The crude product is partitioned between 200 ml of chloroform and 200 ml of cold 1 molar sodium carbonate solution, following which the organic phase is separated from the aqueous phase, dried with magnesium sulfate and evaporated to dryness. The residue is recrystallized twice from methylene chloride/t-butyl methyl ether to yield the pure title compound (mp 126°-127.5° C.).

Workup

  1. temperatureheated to 50° to 55° C. for 5 hours
  2. temperatureThis mixture is cooled to room temperature
  3. filtrationfiltered
  4. washThe residue is washed with THF
  5. customevaporated to dryness
  6. customThe crude product is partitioned between 200 ml of chloroform and 200 ml of cold 1 molar sodium carbonate solution
  7. customis separated from the aqueous phase
  8. dry with materialdried with magnesium sulfate
  9. customevaporated to dryness
  10. customThe residue is recrystallized twice from methylene chloride/t-butyl methyl ether

Sources & evidence

ORD record
ord-4188592ac9664d39bdd54ccaa1a9107a
Source dataset
uspto-grants-1995_01
Patent number
US05378728

Reaction notes

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