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Methylthiouracil → 4(1H)-Pyrimidinone, 2-(((2-(dimethylamino)phenyl)methyl)thio)-6-methyl-

HRID 2247848
ノート
印刷プレビュー

反応式

HRID 2247848 の反応式
[CH3:1][C:2]1[NH:7][C:6](=[S:8])[NH:5][C:4](=[O:9])[CH:3]=1.[Na].N1C=CC(=O)NC1=S.[Cl-].Cl[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH+:28]([CH3:30])[CH3:29]>[O-]CC.[Na+].C(O)C>[CH3:29][N:28]([CH3:30])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH2:21][S:8][C:6]1[NH:5][C:4](=[O:9])[CH:3]=[C:2]([CH3:1])[N:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 667493MethylthiouracilHCID 1269845ThiouracilHCID 5360545SodiumHCID 178486212HCID 178486212、化合物

生成物 1

HCID 1357442584(1H)-Pyrimidinone, 2-(((2-(dimethylamino)phenyl)methyl)thio)-6-methyl-収率 47.7%

試薬・触媒・溶媒 2

HCID 702Ethanol
溶媒
HCID 2723922Sodium ethoxide溶媒

実験手順

355 mg (2.5 mmol) of 6-methyl-2-thiouracil are dissolved in a sodium ethoxide solution prepared from 116 mg (5.05 mmol) of sodium metal and 15 ml of anhydrous ethanol. The mixture is gently warmed to dissolve the thiouracil, then 515 mg (2.5 mmol) of (2-chloromethylphenyl)-dimethylammonium chloride are added and the reaction mixture is refluxed under stirring for 1 hour. Sodium chloride is immediately precipitated from the solution. After evaporation under reduced pressure the residue is taken up in water, extracted 3 times with 20 ml of chloroform each, then the combined organic phase is washed with 20 ml of water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The pale yellow oily residue is rubbed with an 1:1 mixture of benzene and petroleum ether to obtain 287 mg (47.7%) of the title compound as a white crystalline product, m.p.: 151°-153° C.

後処理

  1. temperatureThe mixture is gently warmed
  2. temperaturethe reaction mixture is refluxed
  3. customSodium chloride is immediately precipitated from the solution
  4. customAfter evaporation under reduced pressure the residue
  5. extractionextracted 3 times with 20 ml of chloroform each, then the combined organic phase
  6. washis washed with 20 ml of water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. additionThe pale yellow oily residue is rubbed with an 1:1 mixture of benzene and petroleum ether

出典と根拠

ORDレコード
ord-baa6d9552ea542a68ccfd12b5de6b346
出典データセット
uspto-grants-1991_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05037830

反応ノート

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