4-Nitrophenol → HCID 59424628, compound

HRID 1711001Notes

Reaction equation

HRID 1711001 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:12]=[CH:13][N:14]([CH3:16])[CH:15]=3)[S:10][C:3]=12.[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)([O-:19])=[O:18].C([O-])([O-])=O.[K+].[K+].O(C1C=CC=CC=1)C1C=CC=CC=1>C(Cl)Cl>[CH3:16][N:14]1[CH:15]=[C:11]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[O:26][C:23]3[CH:24]=[CH:25][C:20]([N+:17]([O-:19])=[O:18])=[CH:21][CH:22]=3)[CH:8]=2)[N:12]=[CH:13]1

Participants

6

Reactant 4

HCID 9804-Nitrophenol2×HCID 7583Diphenyl EtherHCID 11430Potassium CarbonateHCID 594245247-Chloro-2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridine

Product 1

HCID 59424628HCID 59424628, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 224 (950 mg, 3.81 mmol), 4-nitrophenol (795 mg, 5.72 mmol), K2CO3 (1.05 g, 7.62 mmol) and Ph2O (5 mL) was stirred at 190° C. for 2 h in a sealed tube, cooled and treated with additional amount of 4-nitrophenol (795 mg, 5.72 mmol). The mixture was stirred for another hour at the same conditions, cooled to room temperature and diluted with DCM. The DCM solution was extracted with 2N HCl; the aqueous phase was collected, basified with concentrated ammonium hydroxide solution (pH˜11) and extracted with EtOAc. The extract was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford 225 (860 mg, 64% yield) as an orange solid. MS (m/z): 353.1 (M+1).

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred for another hour at the same conditions
  3. temperaturecooled to room temperature
  4. extractionThe DCM solution was extracted with 2N HCl
  5. customthe aqueous phase was collected
  6. extractionextracted with EtOAc
  7. dry with materialThe extract was dried over anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9913ec0a32f540b580f02c1be6f4e15b
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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