Sulfamide → 1-(2-Fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

HRID 1818771노트

반응식

HRID 1818771 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=1.[S:16](N)(N)(=[O:18])=[O:17]>COCCOCCOC.CCOCC>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH:15][S:16]1(=[O:18])=[O:17]

참가 물질

5

반응물 2

HCID 82267SulfamideHCID 19039441N1-(2-Fluorophenyl)benzene-1,2-diamine

생성물 1

HCID 468330941-(2-Fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide수율 23.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8150Diglyme용매2회

실험 절차

Dry diglyme (10 mL) was added to a flask equipped with a dropping funnel under a nitrogen atmosphere and brought to a vigorous reflux N-(2-fluorophenyl)benzene-1,2-diamine (1.2 g, 6.0 mmol) and sulfamide (0.69 g, 7.2 mmol) were dissolved in 5 mL of diglyme and placed in the dropping funnel. The mixture was added dropwise to the flask over 15 minutes and then refluxing was continued for an additional 15 minutes. The mixture was cooled to ambient temperature and diluted with ether, washed with water, 2N HCl, water, brine, dried over anhydrous magnesium sulfate, and concentrated. The crude product was purified via Isco chromatography (Redisep, silica, gradient 5-50% (ethyl acetate containing 2% formic acid) in hexane) to afford 1-(2-fluorophenyl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (0.37 g).

후처리

  1. customequipped with a dropping funnel under a nitrogen atmosphere
  2. additionThe mixture was added dropwise to the flask over 15 minutes
  3. temperaturerefluxing
  4. washwashed with water, 2N HCl, water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified via Isco chromatography (Redisep, silica, gradient 5-50% (ethyl acetate containing 2% formic acid) in hexane)

출처 및 근거

ORD 기록
ord-74c91b520f1d4741a148da04c0ec3175
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601722B2

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