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Valinol → 5-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-N-[1-(hydroxymethyl)-2-methylpropyl]-1,2-benzisothiazole-3-carboxamide

HRID 48985
ノート
印刷プレビュー

反応式

HRID 48985 の反応式
[NH2:1][CH:2]([CH:5]([CH3:7])[CH3:6])[CH2:3][OH:4].[CH3:8][N:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][C:12](=[O:19])[N:11]([C:20]2[CH:21]=[CH:22][C:23]3[S:27][N:26]=[C:25]([C:28](Cl)=[O:29])[C:24]=3[CH:31]=2)[C:10]1=[O:32]>O1CCCC1.C(OCC)C>[CH3:8][N:9]1[C:14]([C:15]([F:18])([F:17])[F:16])=[CH:13][C:12](=[O:19])[N:11]([C:20]2[CH:21]=[CH:22][C:23]3[S:27][N:26]=[C:25]([C:28]([NH:1][CH:2]([CH2:3][OH:4])[CH:5]([CH3:7])[CH3:6])=[O:29])[C:24]=3[CH:31]=2)[C:10]1=[O:32]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 79019ValinolHCID 113038335-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxylic acid chloride

生成物 1

HCID 206342735-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-N-[1-(hydroxymethyl)-2-methylpropyl]-1,2-benzisothiazole-3-carboxamide収率 86.2%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒
HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

To a solution of 2-amino-3-methyl-1-butanol (1.39 g, 13.5 mmol) in anhydrous tetrahydrofuran at 0° C. is added dropwise a solution of 5-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxylic acid chloride (2.10 g, 5.39 mmol) in tetrahydrofuran. The resultant mixture is stirred 7.5 hours at ambient temperature, diluted with diethyl ether, washed with 1M aqueous hydrochloric acid, saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is chromatographed on silica gel with hexanes-ethyl acetate to afford the title compound as a solid (2.12 g, 86.2%, mp 120° C.) which is identified by NMR spectral analysis.

後処理

  1. washwashed with 1M aqueous hydrochloric acid, saturated sodium bicarbonate and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is chromatographed on silica gel with hexanes-ethyl acetate

出典と根拠

ORDレコード
ord-76a77cb533724934a7a7dde2e7182af6
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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