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

HRID 266439

반응식

HRID 266439 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-d7ea0a1b46ce450e9e071c7e102e50cb
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05650422

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