p-Toluenesulfonic acid → HCID 16128669, compound

HRID 2266411Notes

Reaction equation

HRID 2266411 reaction equation
O[CH2:2][CH2:3][NH:4][C:5]([C:7]1[N:8]=[CH:9][N:10]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Br:18])[CH:13]=2)[CH:11]=1)=[O:6].C(N(CC)CC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.O>[Br:18][C:14]1[CH:13]=[C:12]([N:10]2[CH:11]=[C:7]([C:5]3[O:6][CH2:2][CH2:3][N:4]=3)[N:8]=[CH:9]2)[CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 86631995HCID 86631995, compound

Product 1

HCID 16128669HCID 16128669, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-(3-Bromo-phenyl)-1H-imidazole-4-carboxylic acid (2-hydroxy-ethyl)-amide (140 mg, 0.45 mmol) was dissolved in CH2Cl2 under argon atmosphere and triethyl amine (321 μL, 2.3 mmol) and para-toluene sulfonic acid (95 mg; 0.5 mmol) were added. After heating for 20 h at reflux the reaction mixture was diluted with water and refluxed for 45 min. After cooling to room temperature the layers were separated and the organic phase was washed with water and dried over Na2SO4. Concentration of the organic layer followed by column chromatography on silica gel with a gradient of 1%-5% MeOH in CH2Cl2 afforded 25 mg (19%) of the title product. HRMS (ESI+): m/z=292.135 [M+H]

Workup

  1. temperatureAfter heating for 20 h
  2. temperatureat reflux the reaction mixture
  3. temperaturerefluxed for 45 min
  4. customwere separated
  5. washthe organic phase was washed with water
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-2e4175f14cd3461fb224ea314e88bed4
Source dataset
uspto-grants-2010_12
Patent number
US07858649B2

Reaction notes

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