2-Fluoroethyl bromide → 1-(2-Fluoroethyl)-5-nitro-1,3-dihydro-2h-2,1-benzisothiazole-2,2-dione

HRID 840196노트

반응식

HRID 840196 반응식
C([O-])(O)=O.[Na+].[N+:6]([C:9]1[CH:10]=[CH:11][C:12]2[NH:16][S:15](=[O:18])(=[O:17])[CH2:14][C:13]=2[CH:19]=1)([O-:8])=[O:7].Br[CH2:21][CH2:22][F:23]>O>[F:23][CH2:22][CH2:21][N:16]1[C:12]2[CH:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:19][C:13]=2[CH2:14][S:15]1(=[O:18])=[O:17]

참가 물질

5

반응물 3

HCID 129822-Fluoroethyl bromideHCID 516892Sodium BicarbonateHCID 155387105-Nitro-1,3-dihydrobenzo[c]isothiazole 2,2-dioxide

생성물 1

HCID 226227621-(2-Fluoroethyl)-5-nitro-1,3-dihydro-2h-2,1-benzisothiazole-2,2-dione수율 67%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

NaHCO3 (0.93 g, 11.0 mmol) is dissolved in H2O (15 mL) and 5-Nitro-1,3-dihydro-2H-2,1-benzisothiazole-2,2-dione (1) (1.90 g, 8.9 mmol) is added with stirring. The mixture is heated to 80° C. for 0.5 hrs and a yellow solid formed. The mixture is cooled to 0° C. and filtered. The solid is washed with cold H2O (15 mL) then with cold EtOH (25 mL). The yellow solid thus obtained is dried under high vacuum then dissolved in dry DMF (15 mL). 1-Bromo-2-fluoroethane (1.52 mL, 20.0 mmol) is added and the solution heated to 100° C. for 4 hrs. The solution is cooled to room temperature then poured into ice water (50 mL). The solid is collected by filtration and gave crystals (1.55 g, 67%) after recrystallization from EtOH. Mp 142-4° C. HRMS (FAB) calcd for C9H9FN2O4S +NA1 283.0165, found 283.0166.

후처리

  1. customa yellow solid formed
  2. temperatureThe mixture is cooled to 0° C.
  3. filtrationfiltered
  4. washThe solid is washed with cold H2O (15 mL)
  5. customThe yellow solid thus obtained
  6. customis dried under high vacuum
  7. dissolutionthen dissolved in dry DMF (15 mL)
  8. temperaturethe solution heated to 100° C. for 4 hrs
  9. temperatureThe solution is cooled to room temperature
  10. filtrationThe solid is collected by filtration

출처 및 근거

ORD 기록
ord-694c4096000c4d0cbab2205b160e4118
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06365612B2

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