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

HRID 1593028ノート

反応式

HRID 1593028 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1e3dc291658d4db0ad27175201ce5268
出典データセット
uspto-grants-2007_11
特許番号
US07294650B2

反応ノート

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