Ethyl Acetate → 4-{3-[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-thioureido}-benzoic acid

HRID 25493

반응식

HRID 25493 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:19][CH3:20])=[C:16]([NH2:18])[CH:17]=1)=[CH:5]2.[C:21]([C:24]1[CH:29]=[CH:28][C:27]([N:30]=[C:31]=[S:32])=[CH:26][CH:25]=1)([OH:23])=[O:22].C(OCC)(=O)C>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][C:6]([C:12]1[CH:13]=[CH:14][C:15]([O:19][CH3:20])=[C:16]([NH:18][C:31](=[S:32])[NH:30][C:27]3[CH:26]=[CH:25][C:24]([C:21]([OH:23])=[O:22])=[CH:29][CH:28]=3)[CH:17]=1)=[CH:5]2

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 2429464-Isothiocyanatobenzoic acid2회HCID 99434395-(5,6-difluoro1H-indol-2-yl)-2-methoxy-phenylamine2회

생성물 1

HCID 101150264-{3-[5-(5,6-Difluoro-1H-indol-2-yl)-2-methoxy-phenyl]-thioureido}-benzoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

The product from Example 3, 5-(5,6-difluoro-1H-indol-2-yl)-2-methoxy-phenylamine, (0.274 g, 1.0 mmol) was mixed with 4-carboxyphenyl isothiocyanate (0.183 g, 1.0 mmol) in tetrahydrofuran (10 mL) and was heated briefly to 50° C. and then allowed to stand overnight at room temperature. The tetrahydrofuran was boiled off on the rotary evaporator (no vacuum) to give a solid. Ethyl acetate (5 mL) was added, and the mixture was allowed to stand overnight at room temperature. The insoluble material was collected by filtration and was a mixture. All material from the reaction mixture was taken up in tetrahydrofuran/ethyl acetate and more 4-carboxyphenyl isothiocyanate (0.020 g, 0.11 mmol) was added and the solvent was boiled off on the rotary evaporator. Ethyl acetate was added to the solid and the mixture allowed to stand overnight at room temperature. The insoluble material was collected by filtration (0.191 g), mp 201-203° C.

후처리

  1. customThe tetrahydrofuran was boiled off on the rotary evaporator (no vacuum)
  2. customto give a solid
  3. waitto stand overnight at room temperature
  4. filtrationThe insoluble material was collected by filtration
  5. customthe solvent was boiled off on the rotary evaporator
  6. additionEthyl acetate was added to the solid
  7. waitto stand overnight at room temperature
  8. filtrationThe insoluble material was collected by filtration (0.191 g), mp 201-203° C.

출처 및 근거

ORD 기록
ord-0bb20bfbad2d47d092416d18cf09c6c3
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858739B2

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