Hydrochloric Acid → [3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methanone

HRID 1258589ノート

反応式

HRID 1258589 の反応式
[CH3:1][N:2]1[CH:6]=[N:5][N:4]=[N:3]1.C([Mg]Cl)(C)C.CON(C)[C:15](=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([S:22][CH3:23])[CH:17]=1.Cl>C1COCC1>[CH3:23][S:22][C:18]1[CH:17]=[C:16]([C:15]([C:6]2[N:2]([CH3:1])[N:3]=[N:4][N:5]=2)=[O:24])[CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1401231H-Tetrazole, 1-methyl-HCID 22321956N-methoxy-N-methyl-3-(methylthio)benzamideHCID 178418918HCID 178418918、化合物

生成物 1

HCID 67189850[3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methanone収率 43%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a stirred solution of 1-methyl-1H-tetrazole (4.20 g, 50 mmol) in anhydrous THF (200 mL), cooled to 0° C. with a brine/ice bath, was added dropwise a solution of isopropylmagnesium chloride (2 M in THF, 30 mL, 60.2 mmol). After the addition was over, the resulting cloudy suspension was stirred for 15 min at 0° C. A solution of N-methoxy-N-methyl-3-(methylsulfanyl)benzamide (10.2 g, 39 mmol) in THF (80 mL) was then added dropwise while keeping the internal temperature below 5° C. The reaction mixture was then allowed to warm up and stirred overnight at room temperature. Aq. HCl (1 M, 65 mL) was added to the reaction mixture, the layers were separated, the water phase was extracted with ethyl acetate (3×50 mL) and the combined organic layers were dried over MgSO4. Purification on silica gel afforded [3-(methylsulfanyl)phenyl](1-methyl-1H-tetrazol-5-yl)methanone as a yellow solid [5.95 g, yield 43%; HPLC/MS: m/z=235 (M+H); logP(HCOOH)=2.52].

後処理

  1. additionAfter the addition
  2. customthe internal temperature below 5° C
  3. temperatureto warm up
  4. stirringstirred overnight at room temperature
  5. customthe layers were separated
  6. extractionthe water phase was extracted with ethyl acetate (3×50 mL)
  7. dry with materialthe combined organic layers were dried over MgSO4
  8. customPurification on silica gel

出典と根拠

ORDレコード
ord-40431746223d4e5c84d0bbbccb48f7e1
出典データセット
uspto-grants-2013_06
特許番号
US08466176B2

反応ノート

読み込み中…