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Dichloromethane → Tert-butyl 2-(4-(4-((2,4-dichlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)propanoate

HRID 453553
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HRID 453553 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:6]=[CH:7][C:8]=1F)#[N:2].[Cl:19][C:20]1[CH:37]=[CH:36][C:23]([CH2:24][CH2:25][NH:26][C:27](=[O:35])[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:44]CCl>CS(C)=O>[Cl:44][C:22]1[CH:21]=[C:20]([Cl:19])[CH:37]=[CH:36][C:23]=1[CH2:24][CH2:25][NH:26][C:27]([C:28]1[CH:33]=[CH:32][C:31]([O:34][C:8]2[CH:7]=[CH:6][C:5]([CH:10]([CH3:18])[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][C:3]=2[C:1]#[N:2])=[CH:30][CH:29]=1)=[O:35]
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참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 60628097N-(4-chlorophenethyl)-4-hydroxybenzamideHCID 68467119Tert-butyl 2-(3-cyano-4-fluorophenyl)propanoate

생성물 1

HCID 68466062Tert-butyl 2-(4-(4-((2,4-dichlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)propanoate

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매

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온도
95 °C

실험 절차

A flask was charged with tert-butyl 2-(3-cyano-4-fluorophenyl)propanoate (0.07 g), N-(4-chlorophenethyl)-4-hydroxybenzamide (0.105 g), and potassium carbonate (0.047 g) in 1 ml of DMSO and stirred at 95° C. for one day. The reaction was taken up in dichloromethane and washed with water. The organic layer was collected, dried over MgSO4, filtered, and concentrated. The crude material was purified by silica gel chromatography, eluting with a solvent system of 5%-80% ethyl acetate/hexanes gave tert-butyl 2-(4-(4-((2,4-dichlorophenethyl)carbamoyl)phenoxy)-3-cyanophenyl)propanoate (0.102 g).

후처리

  1. washwashed with water
  2. customThe organic layer was collected
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with a solvent system of 5%-80% ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-5b81197b8d634a7cbf4712bfae5cada5
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08492437B2

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