p-nitrophenol sodium salt → 2-[(4-Nitrophenoxy)methyl]-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trione

HRID 266439

反応式

HRID 266439 の反応式
Cl[CH2:2][N:3]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[S:4]1(=[O:6])=[O:5].[N+:15]([C:18]1[CH:24]=[CH:23][C:21]([O-:22])=[CH:20][CH:19]=1)([O-:17])=[O:16].[Na+]>C1COCC1>[N+:15]([C:18]1[CH:24]=[CH:23][C:21]([O:22][CH2:2][N:3]2[C:13](=[O:14])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:4]2(=[O:6])=[O:5])=[CH:20][CH:19]=1)([O-:17])=[O:16]

参加物

4

反応物 2

HCID 13214p-nitrophenol sodium saltHCID 23024352-(Chloromethyl)-2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione

生成物 1

HCID 149579152-[(4-Nitrophenoxy)methyl]-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trione収率 21.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

A mixture of 2-(chloromethyl) saccharin (3 g, 12.9 mmol) and sodium p-nitrophenoxide (2.55 g, 12.9 mmol) in THF (50 ml) was heated overnight at 50° C. and then refluxed for 45 minutes. The reaction mixture was cooled, poured into a dilute sodium bicarbonate/ice solution and extracted twice with ethyl acetate. The combined organic extracts were washed with sodium bicarbonate solution and water, dried (Na2SO4), and taken to dryness in vacuo. Chromatography (silica gel; MDC) afforded an oil that was crystallized from hot cyclohexane/ether. The resultant solid was recrystallized from ethanol to afford 0.92 g of 2-(4-nitrophenoxymethyl)-saccharin as white shiny platelets, mp 162°-164° C. 1H nmr (90 MHz, CDCl3, DMSO-d6):5.95 (2H, s). FDMS m/e 334 (M+).

後処理

  1. temperaturerefluxed for 45 minutes
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organic extracts were washed with sodium bicarbonate solution and water
  5. dry with materialdried (Na2SO4)
  6. customChromatography (silica gel; MDC) afforded an oil that
  7. customwas crystallized from hot cyclohexane/ether
  8. customThe resultant solid was recrystallized from ethanol

出典と根拠

ORDレコード
ord-d7ea0a1b46ce450e9e071c7e102e50cb
出典データセット
uspto-grants-1997_07
特許番号
US05650422

関連ノート

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