Sulfamethazine → 4-Benzylamino-N-(4,6-dimethylpyrimidin-2-yl)-benzenesulfonamide

HRID 1884821

反応式

HRID 1884821 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH3:19])[N:5]=[C:6]([NH:8][S:9]([C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)(=[O:11])=[O:10])[N:7]=1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CO>[CH2:20]([NH:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][C:6]2[N:5]=[C:4]([CH3:19])[CH:3]=[C:2]([CH3:1])[N:7]=2)(=[O:11])=[O:10])=[CH:13][CH:14]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

5

反応物 3

HCID 5327SulfamethazineHCID 7498Benzyl BromideHCID 10796Cesium carbonate

生成物 1

HCID 101558934-Benzylamino-N-(4,6-dimethylpyrimidin-2-yl)-benzenesulfonamide

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

100 mg (0.36 mmol) sulfamethazine and 70.8 μl (0.60 mmol) benzyl bromide were dissolved in 4 ml methanol. Caesium carbonate (113.4 mg, 0.35 mmol) was added and solution was refluxed overnight with stirring. The reaction mixture was then evaporated to dryness, and purified on silica using gradient elution (chloroform to 2% methanol in chloroform) to obtain white crystals in a yield similar to that described in example 1 for step III. 1H NMR (CDCl3, 500 MHz): 7.93 (2H, m), 7.31 (5H, m), 6.58 (3H, m), 4.36 (2H, s), 2.34 (6H, s); MS (ESI+): m/z 369 (M+H)+.

後処理

  1. temperaturesolution was refluxed overnight
  2. customThe reaction mixture was then evaporated to dryness
  3. custompurified on silica using gradient elution (chloroform to 2% methanol in chloroform)
  4. customto obtain white crystals in a yield similar to

出典と根拠

ORDレコード
ord-cbdbf0c9d743492b9dc28d251d1b0053
出典データセット
uspto-grants-2004_07
特許番号
US06767909B2

関連ノート

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