1-(4-Iodophenyl)ethan-1-one → HCID 54008310, compound

HRID 861415Notes

Reaction equation

HRID 861415 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([I:10])=[CH:6][CH:5]=1)=[O:3].CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[I:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH:1]=[CH:13][N:14]([CH3:16])[CH3:15])=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 728691-(4-Iodophenyl)ethan-1-oneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 54008310HCID 54008310, compound

Procedure

A solution of 4-iodoacetophenone (6.15 g) in N,N-dimethylformamide dimethyl acetal (6.5 ml) was heated at reflux for 8 hours. The reaction mixture was evaporated and the solid residue was recrystallised from acetonitrile to give 1-(4-iodophenyl)-3-dimethylamino-2-propen-1-one (4.38 g), as a solid, m.p. 117°-118° C.; NMR(CDCl3): 2.60-3.50(6H,br.d), 5.64(1H,d), 7.62(2H,d), 7.77(2H,d) and 7.80(1H,d), m/z 302(M+H). A mixture of 1-(4-iodophenyl)-3-dimethylamino-2-propen-1-one (3.0 g) and hydroxylamine hydrochloride (0.73 g) in 1:1 dioxane/water (30 ml) was stirred at ambient temperature for 48 hours. Addition of water gave a solid which was collected by filtration, washed with water, and purified by flash column chromagatography on silica gel using 1:1 (v/v) ethyl acetate/pentane as eluent. There was thus obtained 5-(4-iodophenyl)-isoxazole (0.6 g); microanalysis found: C, 39.4; H, 2.3; N, 4.8%; C9H6INO requires: C, 39.9; H, 2.23; N, 5.17%; NMR(CDCl3): 6.54(1H,d), 7.52(2H,d), 7.83(2H,d) and 8.28(1H,d); m/e 272(M+H).

Workup

  1. temperatureat reflux for 8 hours
  2. customThe reaction mixture was evaporated
  3. customthe solid residue was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-d9208b9b9f55492cb8f2ba98c54033c7
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

Loading…