HCID 20637206, compound → 1-(3,4-Dichloro-5-isothiazolyl)-3-(4-hydroxyphenyl)-1,3-propanedione

HRID 49408Notes

Reaction equation

HRID 49408 reaction equation
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8](=[O:23])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18]COCC)=[CH:14][CH:13]=2)=[O:11])[S:4][N:3]=1>C(O)(C)C.O1CCCC1>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([C:8](=[O:23])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[O:11])[S:4][N:3]=1

Participants

4

Reactant 1

HCID 20637206HCID 20637206, compound

Product 1

HCID 121153731-(3,4-Dichloro-5-isothiazolyl)-3-(4-hydroxyphenyl)-1,3-propanedioneYield 88.8%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3,4-dichloro-5-isothiazolyl)-3-(4-ethoxymethoxyphenyl)-1,3-propanedione (1.20 g) in a mixture of isopropanol (20 ml) and tetrahydrofuran (20 ml) concentrated hydrochloric acid (3.40 g) was added at room temperature and the mixture was stirred for 12 hours. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluent hexane:ethyl acetate=50:50) to obtain 1-(3,4-dichloro-5-isothiazolyl)-3-(4-hydroxyphenyl)-1,3-propanedione (0.90 g). mp 224-227° C.

Workup

  1. additionwas added at room temperature
  2. distillationAfter distilling off the solvent under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (eluent hexane:ethyl acetate=50:50)

Sources & evidence

ORD record
ord-d4143b699b0347f1a84a33aa14302ec3
Source dataset
uspto-grants-2004_03
Patent number
US06706748B2

Reaction notes

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