Potassium Iodide → 6-Iodo-2,3-dihydro-1-benzothiophene 1,1-dioxide

HRID 1593028Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1593028
[S:1]1(=[O:12])(=[O:11])[C:5]2[CH:6]=[C:7](N)[CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.N([O-])=O.[Na+].[I-:17].[K+]>O>[I:17][C:7]1[CH:8]=[CH:9][C:4]2[CH2:3][CH2:2][S:1](=[O:12])(=[O:11])[C:5]=2[CH:6]=1

Komponenten

5

Edukt 3

HCID 4875Potassium IodideHCID 122853256-Amino-2,3-dihydro-1lambda6-benzothiophene-1,1-dioneHCID 23668193Sodium Nitrite

Produkt 1

HCID 585219066-Iodo-2,3-dihydro-1-benzothiophene 1,1-dioxideAusbeute 37,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A mixture of 2,3-dihydro-1-benzothiophen-6-amine 1,1-dioxide (1.1 g) 2M hydrochloric acid (14 ml) was cooled in an ice-bath. Sodium nitrite (355 mg) in water (5 ml) was added dropwise and the mixture was stirred for 15 min before aqueous potassium iodide (830 mg) was added. The mixture was stirred overnight, before it was heated to 65° C. for 0.5 h. The mixture was cooled to 20° C. and extracted into ethyl acetate. The organic solution was washed with aqueous sodium metabisulfite solution, brine, dried and purified on two SPE silica cartridges (10 g) eluting with dichloromethane, diethyl ether and ethyl acetate. The dichloromethane fractions were combined and evaporated to give the title compound (550 mg) LCMS RT=2.65 min.

Aufarbeitung

  1. temperaturewas cooled in an ice-bath
  2. additionwas added
  3. temperatureThe mixture was cooled to 20° C.
  4. extractionextracted into ethyl acetate
  5. washThe organic solution was washed with aqueous sodium metabisulfite solution, brine
  6. customdried
  7. custompurified on two SPE silica cartridges (10 g)
  8. washeluting with dichloromethane, diethyl ether and ethyl acetate
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1e3dc291658d4db0ad27175201ce5268
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07294650B2

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