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Nitrogen → 3-[tert-Butyl-(2,4-dichloro-benzoyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

HRID 2193920
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인쇄 미리보기

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HRID 2193920 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][C:9]=1[NH:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:4].N#N.[Cl:23][C:24]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>ClC(Cl)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][C:9]=1[N:10]([C:11]([CH3:14])([CH3:12])[CH3:13])[C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:31]([Cl:33])=[CH:32][C:24]=1[Cl:23])=[O:4]
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참가 물질

5

반응물 3

HCID 947NitrogenHCID 666452,4-Dichlorobenzoyl chlorideHCID 207757713-tert-Butylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester

생성물 1

HCID 207757533-[tert-Butyl-(2,4-dichloro-benzoyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester수율 69.2%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of 3-tert-Butylamino-5-phenyl-thiophene-2-carboxylic acid methyl ester (100 mg, 0.35 mmol) in dichloroethane (10 ml) in an atmosphere of N2 was added 2,4-dichloro-benzoyl chloride (79 mg, 0.38 mmol). The reaction mixture was stirred for 16 h at reflux. Then, the solvents were removed and the residue was purified by flash chromatography (9:1 Hexane/EtOAc) to obtain 112 mg (69%) of 3-[tert-Butyl-(2,4-dichloro-benzoyl)-amino]-5-phenyl-thiophene-2-carboxylic acid methyl ester. NMR 1H (CDCl3, 400 MHz): 7.50 ppm (m, 2H, Haro); 7.44-7.34 ppm (m, 3H, Haro); 7.27 ppm (s, 1H, Haro); 7.18 ppm (dl, 1H, Haro); 7.14 ppm (d, 1H, Haro); 7.00 ppm (dd, 1H, Haro); 3.93 ppm (s, 3H); 1.56 ppm (s, 9H).

후처리

  1. temperatureat reflux
  2. customThen, the solvents were removed
  3. customthe residue was purified by flash chromatography (9:1 Hexane/EtOAc)

출처 및 근거

ORD 기록
ord-2a62e448f80b499dbfd3a4ee91725468
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08329924B2

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