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

HRID 1593028노트

반응식

HRID 1593028 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1e3dc291658d4db0ad27175201ce5268
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07294650B2

반응 노트

불러오는 중…