m-Chloroperbenzoic acid → 2-Pyridinecarboxamide, N-methyl-4-[[2-(methylsulfinyl)-6-benzothiazolyl]oxy]-

HRID 1988423

反応式

HRID 1988423 の反応式
[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:22]=[CH:21][C:15]3[N:16]=[C:17]([S:19][CH3:20])[S:18][C:14]=3[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4].C1C=C(Cl)C=C(C(OO)=[O:31])C=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][NH:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:22]=[CH:21][C:15]3[N:16]=[C:17]([S:19]([CH3:20])=[O:31])[S:18][C:14]=3[CH:13]=2)[CH:8]=[CH:7][N:6]=1)=[O:4]

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 57725401N-Methyl-4-((2-(methylthio)benzo[d]thiazol-6-yl)oxy)picolinamide

生成物 1

HCID 577253932-Pyridinecarboxamide, N-methyl-4-[[2-(methylsulfinyl)-6-benzothiazolyl]oxy]-

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To the solution of 4-(2-methylsulfanyl-benzothiazol-6-yloxy)-pyridine-2-carboxylic acid methylamide from step 3 (3.88 g, 11.72 mmol, 1.0 eq) in DCM (20 mL) at 0° C., was added MCPBA (77%, 2.88 g, 1. eq). The mixture was stirred at this temperature for one hour. Saturated sodium bicarbonate solution (100 mL) was added. The aqueous layer was extracted with DCM (3×150 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated in vacuo to yield 4-(2-methanesulfinyl-benzothiazol-6-yloxy)-pyridine-2-carboxylic acid methylamide as white powder in quantitative yields. The crude product was used in the next step without purification. M+H=348.0.

後処理

  1. extractionThe aqueous layer was extracted with DCM (3×150 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

出典と根拠

ORDレコード
ord-a33360f05efd485dae818dde4283eac1
出典データセット
uspto-grants-2009_06
特許番号
US07553854B2

関連ノート

読み込み中…