Potassium Iodide → Ethyl 2-(4-cyanomethyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl)acetate

HRID 1655891ノート

反応式

HRID 1655891 の反応式
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[S:4][CH:3]1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].Br[CH2:19][C:20]#[N:21].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CS(C)=O>[C:20]([CH2:19][N:7]1[C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[S:4][CH:3]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:2]1=[O:1])#[N:21]

参加物

7

反応物 5

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 25517Ammonium ChlorideHCID 2778792Ethyl 2-(3-oxo-3,4-dihydro-2h-1,4-benzothiazin-2-yl)acetate

生成物 1

HCID 10062806Ethyl 2-(4-cyanomethyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl)acetate収率 82.8%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

After 1.82 g of ethyl 2-(3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl)acetate, 1.31 g of bromoacetonitrile and 146 mg of potassium iodide were dissolved in dimethylsulfoxide (18 ml), 1.50 g of potassium carbonate was added to the solution. The mixture was stirred at room temperature for 40 hours. After saturated ammonium chloride aqueous solution was added to the reaction mixture, the mixture was extracted with ethyl acetate. After the organic phase was washed with saturated sodium chloride aqueous solution, the organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off. The resulting semicrystalline residue was dissolved in benzene. After insoluble matters were filtered off, the solvent was distilled off. Isopropyl ether was added to the residue for crystallization to give 1.74 g of the title compound. The structural formula and physical data of this compound are shown in Table 5.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washAfter the organic phase was washed with saturated sodium chloride aqueous solution
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. dissolutionThe resulting semicrystalline residue was dissolved in benzene
  6. filtrationAfter insoluble matters were filtered off
  7. distillationthe solvent was distilled off
  8. additionIsopropyl ether was added to the residue for crystallization

出典と根拠

ORDレコード
ord-6063f0cf426240e584fe1b27bf8da548
出典データセット
uspto-grants-1993_10
特許番号
US05252571

反応ノート

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