Dimethyl Sulfoxide → HCID 22936466, compound

HRID 853342Notes

Reaction equation

HRID 853342 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 aqueous ammonium chloride solution 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 aqueous ammonium chloride solution
  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-8f1b6e9914c1450da96a364649b053e1
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

Loading…