Potassium Hydroxide → HCID 9840367, compound

HRID 1005968Notes

Reaction equation

HRID 1005968 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][C:9]1[NH:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1.Cl.Br[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1.[OH-].[K+].C1OCCOCCOCCOCCOCCOC1>O.CS(C)=O>[N:23]1[CH:24]=[CH:25][C:20]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][S:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[N:10]=2)=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 2855718-Crown-6HCID 881004-Bromopyridinium chlorideHCID 19030808HCID 19030808, compound

Product 1

HCID 9840367HCID 9840367, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

0.5 g of the compound obtained in Example 26a, 0.4 g of 4-bromopyridine hydrochloride, 0.38 g of potassium hydroxide and 0.2 g of 18-crown-6-ether were added to 10 ml of DMSO and the mixture was heated to 150° C. with stirring for 6 hours. After cooling, the reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with water and dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:methylene chloride=1:3) and crystallized from acetonitrile to obtain 0.14 g of the title compound (yield: 22%).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (ethyl acetate:methylene chloride=1:3)
  7. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-59829821a42b48e3b3f1823929244d66
Source dataset
uspto-grants-2004_09
Patent number
US06787561B1

Reaction notes

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