Methyl iodide → Ethyl 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate

HRID 277380

反応式

HRID 277380 の反応式
[O:1]=[C:2]1[NH:7][C:6]([C:8]([F:11])([F:10])[F:9])=[CH:5][C:4](=[O:12])[N:3]1[C:13]1[CH:14]=[CH:15][C:16]2[S:20][N:19]=[C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]=2[CH:27]=1.[C:28](=O)([O-])[O-].[K+].[K+].IC.C(OCC)(=O)C>CN(C)C=O.O>[CH3:28][N:7]1[C:6]([C:8]([F:9])([F:10])[F:11])=[CH:5][C:4](=[O:12])[N:3]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]=3[CH:27]=2)[C:2]1=[O:1]

参加物

7

反応物 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 10960337Ethyl 5-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate

生成物 1

HCID 11729347Ethyl 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate収率 54.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of ethyl 5-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate (0.643 g, 0.00160 mol) and potassium carbonate (0.243 g, 0.00170 mol) in N,N-dimethylformamide is stirred at room temperature for 90 minutes, treated with iodomethane (0.320 mL, 0.00500 mol), stirred at room temperature overnight, and diluted with water. The resultant aqueous mixture is extracted with methylene chloride. The organic extract is washed with water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a brown oil. Column chromatography of the oil using silica gel and a 10% ethyl acetate in hexanes solution gives the title product as a tan solid (0.362 g, mp 150-152° C.).

後処理

  1. stirringstirred at room temperature overnight
  2. extractionThe resultant aqueous mixture is extracted with methylene chloride
  3. extractionThe organic extract
  4. washis washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a brown oil

出典と根拠

ORDレコード
ord-42d95f5ce4a640a69f6c8a8264c1801c
出典データセット
uspto-grants-2002_03
特許番号
US06355796B1

関連ノート

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