Pyridine → (3-Bromothien-2-yl) (3-methoxyphenyl)methanone oxime

HRID 8641

Reaction equation

HRID 8641 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)=O.Cl.[NH2:18][OH:19].N1C=CC=CC=1.C(Cl)Cl>CCCCCC>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)=[N:18][OH:19]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 443297Hydroxyamine hydrochlorideHCID 21915416(3-Bromothien-2-yl) (3-methoxyphenyl)methanone

Product 1

HCID 72727313(3-Bromothien-2-yl) (3-methoxyphenyl)methanone oximeYield 87%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Stir a mixture of (3-bromothiophen-2-yl)-(3-methoxyphenyl)methanone (7 g, 0.024 mol), hydroxylamine hydrochloride (3.09 g, 0.048 mol) and pyridine (40 mL) overnight at room temperature, and then heat the mixture (100° C.–105° C.) for four hours. TLC (DCM) shows that the reaction is complete. Quench the reaction mixture with water and extract with ether (three times). Wash the ether phase with HCl (3N) and water, dry (MgSO4), filter and concentrate to yield an oil that solidifies. Recrystallize the solid from ether:hexane to obtain the title compound (6.4 g, 87% Yield), m.p. 102–103° C.

Workup

  1. temperatureheat the mixture (100° C.–105° C.) for four hours
  2. customQuench the reaction mixture with water
  3. extractionextract with ether (three times)
  4. washWash the ether phase with HCl (3N) and water
  5. dry with materialdry (MgSO4)
  6. filtrationfilter
  7. concentrationconcentrate
  8. customto yield an oil
  9. customRecrystallize the solid from ether

Sources & evidence

ORD record
ord-6dcbe5d9d92e4048baae54673195caa5
Source dataset
uspto-grants-2006_08
Patent number
US07091199B1

Linked notes

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