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

HRID 843244

反応式

HRID 843244 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24562Silver perchlorate触媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-56a6e7d2feec4b4abb7948634857bc59
出典データセット
uspto-grants-2002_04
特許番号
US06376664B1

関連ノート

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