Dimethyl Sulfoxide → HCID 22936466, compound

HRID 387820Notes

Reaction equation

HRID 387820 reaction equation
[CH:1]1([C:5]([NH:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.[S:22]1[CH:26]=[CH:25][N:24]=[C:23]1[NH:27][C:28](=O)[O:29]C1C=CC=CC=1.CS(C)=O.O>C(OCC)(=O)C>[CH:1]1([C:5]([NH:7][C:8]2[CH:13]=[C:12]([O:14][C:15]3[CH:16]=[CH:17][C:18]([NH:19][C:28]([NH:27][C:23]4[S:22][CH:26]=[CH:25][N:24]=4)=[O:29])=[CH:20][CH:21]=3)[CH:11]=[CH:10][N:9]=2)=[O:6])[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 651148phenyl N-(1,3-thiazol-2-yl)carbamateHCID 22936480HCID 22936480, compound

Product 1

HCID 22936466HCID 22936466, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-(2-Cyclobutanecarbonylaminopyridin-4-yl)oxyaniline (130 mg), phenyl N-(2-thiazolyl)carbamate (110 mg) and dimethylsulfoxide (3 ml) were stirred at 80° C. for 30 minutes. Water and ethyl acetate were added to the reaction solution for extraction, and the ethyl acetate layer was washed 5 times with ammonium chloride water and then dried over magnesium sulfate. The drying agent was filtered off, the solvent was distilled off under reduced pressure, ethyl acetate was added to the residue and the precipitated solid was filtered out to obtain 130 mg of the target substance as a light brown solid.

Workup

  1. washthe ethyl acetate layer was washed 5 times with ammonium chloride water
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe drying agent was filtered off
  4. distillationthe solvent was distilled off under reduced pressure, ethyl acetate
  5. additionwas added to the residue
  6. filtrationthe precipitated solid was filtered out
  7. customto obtain 130 mg of the target substance as a light brown solid

Sources & evidence

ORD record
ord-c3399a4612264e3d906c9f0b7aea30af
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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