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

HRID 1593028Notes

Reaction equation

HRID 1593028 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 585219066-Iodo-2,3-dihydro-1-benzothiophene 1,1-dioxideYield 37.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1e3dc291658d4db0ad27175201ce5268
Source dataset
uspto-grants-2007_11
Patent number
US07294650B2

Reaction notes

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