Thionyl Chloride → 6-Chloro-1-(5-isothiazolyl)-3,4-dihydronaphthalene

HRID 1768636Notes

Reaction equation

HRID 1768636 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](O)([C:16]1[S:20][N:19]=[CH:18][CH:17]=1)[CH2:11][CH2:10][CH2:9]2>C1C=CC=CC=1>[Cl:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12]([C:16]1[S:20][N:19]=[CH:18][CH:17]=1)=[CH:11][CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 189490446-Chloro-1-hydroxy-1-(5-isothiazolyl)-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 189490486-Chloro-1-(5-isothiazolyl)-3,4-dihydronaphthalene

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.072 ml of thionyl chloride is added at room temperature to a solution of 132 mg of 6-chloro-1-hydroxy-1-(5-isothiazolyl)-1,2,3,4-tetrahydronaphthalene (Example 12) in 0.45 ml of benzene, and the mixture is then stirred at 75° for 1.5 hours. The mixture is concentrated under reduced pressure, 0.156 ml of morpholine is added to the resulting resin, and the mixture is stirred at 75° for 2.5 hours. The black suspension is cooled to 2° and treated with 5N HCl which has likewise been pre-cooled. The pH is then adjusted to 8 with solid NaHCO3 and extraction is carried out with chloroform. The organic phase is separated off, dried over sodium sulfate and concentrated. The crude title compound is purified by column chromatography (SiO2, hexane/ethyl acetate 4:1 ) and crystallisation from hexane; 1H-NMR (CDCl3): δ (ppm)=2.44 (m,2H), 2.85 (m,2H), 6.37 (t,1H), 7.14 (m,2H), 7.19 (d,1H), 7.21 (s,1H), 8.49 (d,1H).

Workup

  1. concentrationThe mixture is concentrated under reduced pressure, 0.156 ml of morpholine
  2. additionis added to the resulting resin
  3. stirringthe mixture is stirred at 75° for 2.5 hours
  4. temperatureThe black suspension is cooled to 2°
  5. additiontreated with 5N HCl which
  6. temperaturehas likewise been pre-cooled
  7. extractionThe pH is then adjusted to 8 with solid NaHCO3 and extraction
  8. customThe organic phase is separated off
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated
  11. customThe crude title compound is purified by column chromatography (SiO2, hexane/ethyl acetate 4:1 ) and crystallisation from hexane

Sources & evidence

ORD record
ord-2dfce1e431994312bf3c23179e865b6f
Source dataset
uspto-grants-1995_01
Patent number
US05378721

Reaction notes

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