Acetic Acid → 2-[[4-(Methylthio)phenyl]amino]isonicotinic acid

HRID 452631

反応式

HRID 452631 の反応式
F[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=[O:6].[CH3:11][S:12][C:13]1[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=1.[H-].[Na+].C(O)(=O)C>CN(C)C=O>[CH3:11][S:12][C:13]1[CH:19]=[CH:18][C:16]([NH:17][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=2)[C:5]([OH:7])=[O:6])=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 660384-(Methylthio)anilineHCID 3453602-Fluoroisonicotinic acid

生成物 1

HCID 284003552-[[4-(Methylthio)phenyl]amino]isonicotinic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

To a solution of 2-fluoroisonicotinic acid (620 mg, 4.95 mmol) and 4-(methylthio)aniline (0.984 mL, 8.42 mmol) in N,N-dimethylformamide (20 mL) was added sodium hydride (792 mg, 19.8 mmol), and the resulting mixture was stirred under an argon atmosphere at 85° C. for 5 hr. After cooling, acetic acid (1.2 mL) was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Ethyl acetate and water were added to the residue, the mixture was stirred for 20 min, and the precipitate was collected by filtration to give crude 2-[[4-(methylthio)phenyl]amino]isonicotinic acid.

後処理

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionEthyl acetate and water were added to the residue
  4. stirringthe mixture was stirred for 20 min
  5. filtrationthe precipitate was collected by filtration

出典と根拠

ORDレコード
ord-421b9b0c69434c2cabddaf72f72d3971
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

関連ノート

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