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

HRID 840194ノート

反応式

HRID 840194 の反応式
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]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 155387105-Nitro-1,3-dihydrobenzo[c]isothiazole 2,2-dioxide

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9f89e859229c448b86f79fe7eeaff69b
出典データセット
uspto-grants-2002_04
特許番号
US06365612B2

反応ノート

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