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Ethanethiol → 3-[3-Cyano-4-[(1-pyrrolidinyl)methyl]benzyl]-6-hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene

HRID 1070337
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HRID 1070337 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[CH2:35][N:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1)[CH2:6][C:7]1[C:8]2[CH:29]=[CH:28][C:27]([O:30]C)=[CH:26][C:9]=2[S:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:14][CH:13]=1)#[N:2].C(S)C.[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[CH2:35][N:36]1[CH2:37][CH2:38][CH2:39][CH2:40]1)[CH2:6][C:7]1[C:8]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][C:9]=2[S:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)=[CH:14][CH:13]=1)#[N:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6343EthanethiolHCID 6451240Aluminum(III) ChlorideHCID 211829133-[3-Cyano-4-[(1-pyrrolidinyl)methyl]benzyl]-6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene

생성물 1

HCID 211828733-[3-Cyano-4-[(1-pyrrolidinyl)methyl]benzyl]-6-hydroxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene수율 68%

시약·촉매·용매 1

HCID 6365
1,1-Dichloroethane
용매

실험 절차

3-[3-Cyano-4-[(1-pyrrolidinyl)methyl]benzyl]-6-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene (60 mg, 0.11 mmol) in dichloroethane (4 mL) at 0° C. under argon was treated with ethanethiol (0.1 mL) and aluminum chloride (100 mg) for 3 h before quenching with saturated aqueous sodium bicarbonate solution (10 mL). The stirring was allowed to continue for 1 h at ambient temperature. The resulting mixture was diluted with saturated aqueous sodium bicarbonate solution (50 mL) and extracted with dichloromethane (50 mL×3). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Chromatography with Et3N:MeOH:EtOAc (5:5:90) afforded the title compound as a white foam (40 mg, 68%).

후처리

  1. custombefore quenching with saturated aqueous sodium bicarbonate solution (10 mL)
  2. additionThe resulting mixture was diluted with saturated aqueous sodium bicarbonate solution (50 mL)
  3. extractionextracted with dichloromethane (50 mL×3)
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-706cf5e96c594712920fcd15a7f01479
출처 데이터셋
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06251921B1

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