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Pyridine → (2-Butyl-5-methylsulfanylamino-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone

HRID 1771253
ノート
印刷プレビュー

反応式

HRID 1771253 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][CH2:11][CH2:12][CH3:13])=[C:7]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])=[CH:18][CH:17]=3)=[O:15])[C:6]=2[CH:35]=1.N1C=CC=CC=1.[CH3:42][S:43]Cl>O>[CH2:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([NH:1][S:43][CH3:42])=[CH:35][C:6]=2[C:7]=1[C:14]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:31][CH2:32][CH2:33][CH3:34])=[CH:20][CH:21]=1)=[O:15])[CH2:11][CH2:12][CH3:13]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1049PyridineHCID 138595MethanesulfenylchlorideHCID 11488441(5-Amino-2-butylbenzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone

生成物 1

HCID 71711318(2-Butyl-5-methylsulfanylamino-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone収率 42%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

4.78 g of (5-amino-2-butyl-benzofuran-3-yl)-[4-(3-dibutylamino-propoxy)-phenyl]-methanone (III) (0.01 mol, 1 eq) and 35 mL of pyridine were placed into a flask. The mixture was cooled down to 0° C. and 0.99 g of methanesulfenyl chloride (II) (0.012 mol, 1.2 eq; freshly prepared as described in the above mentioned literature) was added in 10 min. The mixture was stirred at 0° C. for 3 hours and then heated to room temperature and stirred for 6 hours. The mixture was poured into 100 mL of water. The product was extracted with 50 mL of dichloromethane. The organic phase was washed with 30 mL of water. The solvent was evaporated and the product was purified by column chromatography (column: spheric silica (60 Å); eluent: toluene:ethyl acetate=70:30) to obtain 2.2 g of compound (IV) (42%) as a light yellow oil.

後処理

  1. customfreshly prepared
  2. additionwas added in 10 min
  3. temperatureheated to room temperature
  4. stirringstirred for 6 hours
  5. extractionThe product was extracted with 50 mL of dichloromethane
  6. washThe organic phase was washed with 30 mL of water
  7. customThe solvent was evaporated
  8. customthe product was purified by column chromatography (column: spheric silica (60 Å); eluent: toluene:ethyl acetate=70:30)

出典と根拠

ORDレコード
ord-c4fb2175e4de4421b23f3a162ca82f8c
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09249119B2

反応ノート

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