Lawesson's reagent → 4-bromo-2-fluoro-N-methylbenzothioamide

HRID 537177ノート

反応式

HRID 537177 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=O)=[C:4]([F:12])[CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:22])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[S:22])[NH:8][CH3:9])=[C:4]([F:12])[CH:3]=1

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 24694329Benzamide, 4-bromo-2-fluoro-N-methyl-

生成物 1

HCID 866646184-bromo-2-fluoro-N-methylbenzothioamide収率 104.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

反応条件

温度
100 °C

実験手順

A mixture of 4-bromo-2-fluoro-N-methylbenzamide (500 mg, 2 mmol) and Lawesson reagent (872 mg, 2.16 mmol) in toluene (10 mL) was heated to 100° C. and stirred for 4 hours. The reaction was cooled to room temperature, diluted with toluene, and filtered. The filtrate was concentrated and purification of the residue by flash column chromatography (0-20% ethyl acetate/heptanes) gave the title compound (520 mg, 97%) as a yellow solid. +ESI (M+H+1) 250.1; 1H NMR (400 MHz, CDCl3, δ): 8.09 (t, J=8.58 Hz, 1H), 8.03 (br. s., 1H), 7.35 (dd, J=8.19, 2.15 Hz, 1H), 7.27 (dd, J=11.41, 1.85 Hz, 1H), 3.36 (dd, J=4.88, 0.78 Hz, 3H).

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. custompurification of the residue by flash column chromatography (0-20% ethyl acetate/heptanes)

出典と根拠

ORDレコード
ord-44879c267dbf4379b5a3d3b5ddef69f4
出典データセット
uspto-grants-2014_10
特許番号
US08859773B2

反応ノート

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