Hydroxyamine hydrochloride → HCID 73853156, compound

HRID 568518Notes

Reaction equation

HRID 568518 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>[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

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 21915324HCID 21915324, compound

Product 1

HCID 73853156HCID 73853156, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of (3-bromothien-2-yl) (4-methoxyphenyl)methanone PG,47 (2.5 g) and hydroxylamine hydrochloride (1.5 g) and 15 ml of pyridine was stirred at room temperature overnight and then heated at 100°-115° C. for 4 hours. A thin layer chromatography analysis showed the reaction to be complete. The mixture was quenched with water and extracted with ether. The ether phase was washed with 3N hydrochloric acid and water and dried over anhydrous magnesium sulfate. Upon evaporation of the ether, an oil was obtained which crystallized upon standing overnight. The solid was recrystallized from ether/pentane to give a pure crystalline product (2.39 g, m.p. 110°-115° C.).

Workup

  1. temperatureheated at 100°-115° C. for 4 hours
  2. customthe reaction
  3. customThe mixture was quenched with water
  4. extractionextracted with ether
  5. washThe ether phase was washed with 3N hydrochloric acid and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customUpon evaporation of the ether
  8. customan oil was obtained which
  9. customcrystallized
  10. customThe solid was recrystallized from ether/pentane

Sources & evidence

ORD record
ord-018dbae121aa49308c63c00a530d95b6
Source dataset
uspto-grants-1988_03
Patent number
US04728651

Reaction notes

Loading…