2-Chloropyridine → HCID 22675455, compound

HRID 1005963Notes

Reaction equation

HRID 1005963 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[NH:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=1.Cl[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.[OH-].[K+].C1OCCOCCOCCOCCOCC[O:28]C1>O.CS(C)=O>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[O:28][CH:3]([CH3:2])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[NH:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[N:9]=1

Participants

7

Reactant 4

HCID 79772-ChloropyridineHCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 22675416HCID 22675416, compound

Product 1

HCID 22675455HCID 22675455, compoundYield 268.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

218 mg of the compound obtained in Example 16a, 115 mg of 2-chloropyridine, 200 mg of KOH and 50 mg of 18-crown-6-ether were added to 15 ml of DMSO and the mixture was heated to 150° C. for 8 hours. The reaction mixture was cooled, then added with water and extracted with ethyl acetate. The extract was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate) to obtain 150 mg of the title compound (yield: 51%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-900643aa4fe64513b5acb00af66df358
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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