Methanol → HCID 54345226, compound

HRID 1870832Notes

Reaction equation

HRID 1870832 reaction equation
C([NH:9][C:10]([NH:12][C:13]1[O:17][N:16]=[C:15]([CH:18]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:22][CH:21]=2)[CH3:19])[CH:14]=1)=[S:11])(=O)C1C=CC=CC=1.CO.C(=O)([O-])[O-].[K+].[K+].O>O1CCCC1>[CH2:26]([C:23]1[CH:22]=[CH:21][C:20]([CH:18]([C:15]2[CH:14]=[C:13]([NH:12][C:10]([NH2:9])=[S:11])[O:17][N:16]=2)[CH3:19])=[CH:25][CH:24]=1)[CH:27]([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 18693723HCID 18693723, compound

Product 1

HCID 54345226HCID 54345226, compoundYield 448.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

This thiourea (4.65 g) was dissolved in tetrahydrofuran (50 ml) and then methanol (50 ml) and potassium carbonate (3.15 g) were added, after which the mixture was stirred at 50° C. for 5 hours. To the reaction mixture was added a small amount of water, and the resulting mixture was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried over sodium sulfate and thereafter concentrated under reduced pressure, to obtain 3-[1-(4-isobutyl-phenyl)-ethyl]-isoxazol-5-yl-thiourea (15.52 g).

Workup

  1. extractionthe resulting mixture was subjected to extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-068f6c0793364247b5a9371c494787b2
Source dataset
uspto-grants-2000_08
Patent number
US06100260

Reaction notes

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