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

HRID 1274587

반응식

HRID 1274587 반응식
[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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.).

후처리

  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

출처 및 근거

ORD 기록
ord-8529716320824d78aad12efa8a24ab5c
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06156700

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