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Toluene → 3-[3-(3,6-Dihydro-4,6,6-trimethyl-2H-pyran-2-yl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil

HRID 49010
ノート
印刷プレビュー

反応式

HRID 49010 の反応式
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH:21]=[O:22])[C:17]=3[CH:23]=2)[C:3]1=[O:24].[CH3:25][C:26](O)([CH2:28][C:29]([CH3:32])(O)[CH3:30])[CH3:27].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>C(OCC)C.C(OCC)(=O)C.O>[CH3:25][C:26]1[CH2:27][CH:21]([C:18]2[C:17]3[CH:23]=[C:13]([N:4]4[C:5](=[O:12])[CH:6]=[C:7]([C:8]([F:9])([F:10])[F:11])[N:2]([CH3:1])[C:3]4=[O:24])[CH:14]=[CH:15][C:16]=3[S:20][N:19]=2)[O:22][C:29]([CH3:32])([CH3:30])[CH:28]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 1411532,4-Pentanediol, 2,4-dimethyl-HCID 178523685-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehyde

生成物 1

HCID 206342123-[3-(3,6-Dihydro-4,6,6-trimethyl-2H-pyran-2-yl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil収率 31.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehyde(0.500 g, 0.00141 mol), 2,4-dimethyl-2,4-pentanediol (0.260 g, 0.00183 mol), p-toluenesulfonic acid (0.0100 g, 0.000071 mol) and toluene is stirred overnight at reflux with azeotropic removal of water. The mixture is cooled to room temperature, diluted with diethyl ether and ethyl acetate and washed with two prortions of water and brine. The organic layer is dried and concentrated in vacuo to a brown oil, which is chromatographed on silica gel with ethyl acetate-hexanes to afford the title compound as a white solid (0.200 g, 31.4%, mp 88-92° C.) which is characterized by NMR spectral analysis.

後処理

  1. washwashed with two prortions of water and brine
  2. customThe organic layer is dried
  3. concentrationconcentrated in vacuo to a brown oil, which
  4. customis chromatographed on silica gel with ethyl acetate-hexanes

出典と根拠

ORDレコード
ord-ca22450bb37740998ec0ebe68c4f1155
出典データセット
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06706663B2

反応ノート

読み込み中…

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