Pyridine → HCID 15205142, compound

HRID 53128Notes

Reaction equation

HRID 53128 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][C:10](=[O:19])[N:11]=[C:12]3[CH:17]=[C:16](C)[CH:15]=[CH:14][C:13]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Cl)(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1.[Br:32]Br.S(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:32][CH:9]1[CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10]1=[O:19]

Participants

7

Reactant 5

HCID 1049PyridineHCID 24408BromineHCID 24819Phosphorus pentachlorideHCID 19961812HCID 19961812, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 15205142HCID 15205142, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-70 °C

Procedure

To a 200 mL three neck round-bottomed flask equipped with a nitrogen inlet and septum were added 5.48 grams (21.8 mmol) 5-phenyl-8-methyl-2-oxobenzazepine, 100 mL dichloromethane, and 4.55 grams (21.8 mmol) phosphorus pentachloride. After dissolution, 1.85 mL (22.9 mmol) pyridine was added, and the solution cooled to -70° C. To the stirring solution (some precipitate appeared at this temperature, but did not affect the reaction) was added a solution of 1.12 mL (21.8 mmol) bromine in 10 mL methylene chloride dropwise over 20 minutes. The reaction was then allowed to warm quickly (10 minutes) to 0° C., and 50 mL of saturated aqueous sodium bisulfite solution was added. The reaction was then diluted with methylene chloride and allowed to stand under sodium bisulfite solution with periodic shaking for 2 hours, until the organic phase no longer exhibited a reddish color. The organic phase was then dried over sodium sulfate and evaporated. The residue was suspended in methylene chloride and filtered, and the solid dissolved to afford 3.39 grams (47%) of product as a white solid. The filtrate was adsorbed onto silica gel and chromatographed using 7:3 hexane/ethyl acetate as eluant to afford additional product as a white solid, 1.38 g, total 5.14 (71%).

Workup

  1. additionwas added
  2. customthe reaction)
  3. temperatureto warm quickly (10 minutes) to 0° C.
  4. dry with materialThe organic phase was then dried over sodium sulfate
  5. customevaporated
  6. filtrationfiltered
  7. dissolutionthe solid dissolved

Sources & evidence

ORD record
ord-95f6d3ee9a0b49bfab7126a901e7f652
Source dataset
uspto-grants-1997_04
Patent number
US05618811

Reaction notes

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