Hydrochloric Acid → HCID 73853156, compound

HRID 1787522Notes

Reaction equation

HRID 1787522 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][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=O.Cl.[NH2:18][OH:19].N1C=CC=CC=1.Cl>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=[N:18][OH:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 21915324HCID 21915324, compound

Product 1

HCID 73853156HCID 73853156, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Stir a solution of (3-bromothiophen-2-yl)-(4-methoxyphenyl)methanone (19.65 g, 0.066 mol), hydroxylamine hydrochloride (6.89 g, 0.099 mol), and pyridine (30 mL) at 85° C. under nitrogen for five hours. Pour the reaction mixture into a mixture of water (120 mL) and toluene (180 mL), and chill to 0° C. Add concentrated hydrochloric acid (approximately 30 mL) dropwise with cooling to adjust to pH 1-2. Filter the mixture and wash the solid with toluene and water. Separate the phases and extract the acidic aqueous phase with toluene. Wash the combined toluene phases twice with water, dry (Na2SO4), filter and evaporate. Combine the residue from the toluene extracts with the previously obtained solid filter cake, and triturate the mixture with petroleum ether. Filter the mixture and dry in vacuo at 60° C. to give the title compound as a white solid (19.6 g, 95% yield).

Workup

  1. additionPour the reaction mixture
  2. temperaturewith cooling
  3. filtrationFilter the mixture
  4. washwash the solid with toluene and water
  5. customSeparate the phases
  6. extractionextract the acidic aqueous phase with toluene
  7. washWash the combined toluene phases twice with water
  8. dry with materialdry (Na2SO4)
  9. filtrationfilter
  10. customevaporate
  11. filtrationfilter cake
  12. customtriturate the mixture with petroleum ether
  13. filtrationFilter the mixture
  14. customdry in vacuo at 60° C.

Sources & evidence

ORD record
ord-aa4b418806d043eeaf2522ad91cc1841
Source dataset
uspto-grants-2009_03
Patent number
US07511046B2

Reaction notes

Loading…