Triethylamine → HCID 86702349、化合物

HRID 2172539ノート

反応式

HRID 2172539 の反応式
[CH2:1]([O:3][C:4]1[CH2:9][CH2:8]/[C:7](=[CH:10]/O)/[C:6](=[N:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:5]=1)[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[F:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[SH:40]>O1CCCC1.O>[F:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[S:40][CH:10]=[C:7]1[C:6](=[N:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH2:9][CH2:8]1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27370732,4-Difluorobenzene-1-thiolHCID 178466915HCID 178466915、化合物

生成物 1

HCID 86702349HCID 86702349、化合物収率 30.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

100 mg (0.39 mmol) of (Z)-4-ethoxy-2-[(4-methylphenyl)imino]cyclohex-3-en-1-ylidene methanol are dissolved in 10 ml of anhydrous tetrahydrofuran, and 325 μl (2.3 mmol) of triethylamine and 60 μl (0.78 mmol) of methanesulphonyl chloride are added at 0° C. After 30 min of stirring at 25° C., the mixture is once more cooled to 0° C., 40 μl (0.35 mmol) of 2,4-difluorobenzenethiol are added and the mixture is stirred at 25° C. for a further 30 min. The reaction mixture is diluted with water and extracted with ethyl acetate, and the organic phase is washed with saturated aqueous sodium chloride solution and dried over sodium sulphate. Purification of the residue by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate) gives 41 mg of N-(6-{[(2,4-difluorophenyl)sulphanyl]methylene}-3-ethoxycyclohex-2-en-1-ylidene)-4-methylaniline as an isomer mixture (ratio about 1:1).

後処理

  1. temperaturethe mixture is once more cooled to 0° C.
  2. stirringthe mixture is stirred at 25° C. for a further 30 min
  3. extractionextracted with ethyl acetate
  4. washthe organic phase is washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customPurification of the residue by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate)

出典と根拠

ORDレコード
ord-9014e3243714474ba088e8c7a5de79e0
出典データセット
uspto-grants-2015_06
特許番号
US09055743B2

反応ノート

読み込み中…