Methyl iodide → 1-Methyl-5-nitro-1,3-dihydrobenzo[c]isothiazole 2,2-dioxide

HRID 840194노트

반응식

HRID 840194 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].I[CH3:21]>O>[CH3:21][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 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 155387105-Nitro-1,3-dihydrobenzo[c]isothiazole 2,2-dioxide

생성물 1

HCID 155387111-Methyl-5-nitro-1,3-dihydrobenzo[c]isothiazole 2,2-dioxide수율 62.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

NaHCO3 (0.2 g, 2.4 mmol) is dissolved in H2O (3 mL) and 5-Nitro-1,3-dihydro-2H-2,1-benzisothiazole-2,2-dione (1) (0.41 g, 1.9 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 (5 mL) then with cold EtOH (15 mL). The yellow solid thus obtained is dried under high vacuum then dissolved in dry DMF (3.5 mL). Iodomethane (0.15 mL, 2.1 mmol) is added and the solution heated to 100° C. for 2 hrs. The solution is cooled to room temperature then poured into ice water (50 mL). The solid is collected by filtration and gave crystals (0.27 g, 62%) after recrystallization from EtOH. Mp 214-6° C. HRMS (FAB) calcd for C8H8N2O4S +H1 229.0283, found 229.0280.

후처리

  1. customa yellow solid formed
  2. temperatureThe mixture is cooled to 0° C.
  3. filtrationfiltered
  4. washThe solid is washed with cold H2O (5 mL)
  5. customThe yellow solid thus obtained
  6. customis dried under high vacuum
  7. dissolutionthen dissolved in dry DMF (3.5 mL)
  8. temperaturethe solution heated to 100° C. for 2 hrs
  9. temperatureThe solution is cooled to room temperature
  10. filtrationThe solid is collected by filtration

출처 및 근거

ORD 기록
ord-9f89e859229c448b86f79fe7eeaff69b
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06365612B2

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