N-bromobutanimide → 3-[3-[3-(Bromomethyl)-2-thienyl]-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil

HRID 48968ノート

反応式

HRID 48968 の反応式
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[C:11]2[CH:12]=[C:13]([N:16]3[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[N:18]([CH3:27])[C:17]3=[O:28])[CH:14]=[CH:15][C:10]=2[S:9][N:8]=1.[Br:29]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:29][CH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[C:11]2[CH:12]=[C:13]([N:16]3[C:21](=[O:22])[CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[N:18]([CH3:27])[C:17]3=[O:28])[CH:14]=[CH:15][C:10]=2[S:9][N:8]=1

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 206341763-[3-[3-(Methyl)-2-thienyl]-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil

生成物 1

HCID 206342133-[3-[3-(Bromomethyl)-2-thienyl]-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil収率 68.2%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

To a mixture of 3-[3-[3-(methyl)-2-thienyl]-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil(0.420 g, 0.993 mmol) and carbon tetrachloride is added N-bromosuccinimide (0.200 g, 1.12 mmol) and benzoyl peroxide (10.0 mg). The resultant mixture is stirred overnight at reflux, cooled and filtered. The filtrate is concentrated in vacuo and the residue partitioned between water and methylene chloride. The organic layer is washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel with methylene chloride-diethyl ether to afford a pale yellow oil, which is crystallized in diethyl ether to afford the title compound as a cream-colored solid (0.340 g, 68.1%, mp 169° C.(dec)) which is identified by NMR spectral analysis.

後処理

  1. temperatureat reflux
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated in vacuo
  5. customthe residue partitioned between water and methylene chloride
  6. washThe organic layer is washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue is chromatographed on silica gel with methylene chloride-diethyl ether
  10. customto afford a pale yellow oil, which
  11. customis crystallized in diethyl ether

出典と根拠

ORDレコード
ord-b9e0cdb8cde043c4858f325736af3083
出典データセット
uspto-grants-2004_03
特許番号
US06706663B2

反応ノート

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