Methanesulfonic Acid → 2(4-Isoxazol-4-yl-phenoxy)-ethylamine

HRID 413311Notes

Reaction equation

HRID 413311 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:21]=[N:22][O:23][CH:24]=2)=[CH:16][CH:15]=1)C1C=CC=CC=1.CS(O)(=O)=O.[OH-].[Na+]>C(Cl)Cl.O>[O:23]1[CH:24]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][CH2:12][CH2:11][NH2:10])=[CH:15][CH:16]=2)[CH:21]=[N:22]1

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 20587952HCID 20587952, compound

Product 1

HCID 185329642(4-Isoxazol-4-yl-phenoxy)-ethylamineYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
35 °C

Procedure

[2-(4-Isoxazol-4-yl-phenoxy)-ethyl]-carbamic acid benzyl ester (1.00 g, 2.81 mmol) was dissolved in methylene chloride (14 ml) and methanesulfonic acid (2.73 ml, 42.2 mmol) was added. The resulting mixture was heated to about 35° C. for about two hours, and was then diluted with methylene chloride and water. The pH of the mixture was adjusted to about 12 with 5N sodium hydroxide, and the mixture was extracted with methylene chloride. The combined extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by column chromatography (20% methanol/methylene chloride) to afford 202 mg (53% yield) of the desired amine. LRMS ([M+H]+)=205.3.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude product was purified by column chromatography (20% methanol/methylene chloride)

Sources & evidence

ORD record
ord-0083f4c3355f405f89f06b0a90b79be4
Source dataset
uspto-grants-2003_05
Patent number
US06566377B2

Reaction notes

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