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

HRID 1771253
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HRID 1771253 반응식
[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]
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c4fb2175e4de4421b23f3a162ca82f8c
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09249119B2

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