Water → (2,1,3-Benzothiadiazol-4-yl)methanol

HRID 843244

반응식

HRID 843244 반응식
Br[CH2:2][C:3]1[C:11]2[C:7](=[N:8][S:9][N:10]=2)[CH:6]=[CH:5][CH:4]=1.[OH2:12]>O1CCOCC1.Cl([O-])(=O)(=O)=O.[Ag+]>[OH:12][CH2:2][C:3]1[C:11]2[C:7](=[N:8][S:9][N:10]=2)[CH:6]=[CH:5][CH:4]=1

참가 물질

5

반응물 2

HCID 962WaterHCID 27762864-(Bromomethyl)-2,1,3-benzothiadiazole

생성물 1

HCID 10012273(2,1,3-Benzothiadiazol-4-yl)methanol수율 63%

시약·촉매·용매 2

HCID 24562Silver perchlorate촉매HCID 312751,4-Dioxane용매

실험 절차

A solution of silver perchlorate (4.75 g, 23 mmol) in water (10 mL) was added to a solution of 4-bromomethyl-2,1,3-benzothiadiazole (4.38 g, 19 mmol) in 1,4-dioxane. The mixture was refluxed for 4 hours to afford a light-yellow suspension. After cooling to room temperature, the precipitate was filtered off through a pad of celite and washed with CH2Cl2. The filtrate was washed with water and brine, dried over Na2SO4. Concentration using a rotary evaporator and subsequent column chromatography on silica gel using hexane/ethyl acetate (5:1) as the eluent afforded 4-hydroxymethyl-2,1,3-benzothiadiazole (2.0 g, 63%) as a light-yellow solid. Rf=0.23 (hexane/ethyl acetate=5:1); 1H NMR (200 MHz, CDCl3) δ2.73 (t,J=6.4 Hz, 1H), 5.18 (d,J=6.4 Hz, 2H), 7.58 (m, 2H), 7.94 (m, 1H); HRMS:Calcd. for C7H6N2OS 166.0201, found 166.0219.

후처리

  1. temperatureThe mixture was refluxed for 4 hours
  2. customto afford a light-yellow suspension
  3. filtrationthe precipitate was filtered off through a pad of celite
  4. washwashed with CH2Cl2
  5. washThe filtrate was washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationConcentration
  8. customa rotary evaporator and subsequent column chromatography on silica gel

출처 및 근거

ORD 기록
ord-56a6e7d2feec4b4abb7948634857bc59
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06376664B1

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