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p-Toluenesulfonic acid monohydrate → Methyl 4-[(2-{1-[2-bromo-5-(4-t-butylphenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)carbonyl]benzoate

HRID 2103895
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HRID 2103895 반응식
[Br:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=2)=[C:5]([OH:10])[C:6]=1[C:7]([CH3:9])=O.[NH:21]([C:23](CC1C=CC(C([O-])=O)=CC=1)=[O:24])[NH2:22].[OH2:35].S([C:40]1[CH:46]=[CH:45][C:43]([CH3:44])=[CH:42][CH:41]=1)(O)(=O)=O.C(Cl)(Cl)Cl.[C:51](OCC)(=[O:53])C>C(O)(C)C>[Br:1][C:2]1[S:3][C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=2)=[C:5]([OH:10])[C:6]=1[C:7](=[N:22][NH:21][C:23]([C:40]1[CH:46]=[CH:45][C:43]([C:44]([O:53][CH3:51])=[O:35])=[CH:42][CH:41]=1)=[O:24])[CH3:9]
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참가 물질

6

반응물 4

HCID 521998p-Toluenesulfonic acid monohydrateHCID 21584013Chloroform ethylacetateHCID 670504602-Bromo-5-(4-t-butylphenyl)-4-hydroxy-3-methylcarbonylthiopheneHCID 1317275854-Hydrazinocarbonylmethylbenzoate

생성물 1

HCID 72360005Methyl 4-[(2-{1-[2-bromo-5-(4-t-butylphenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)carbonyl]benzoate수율 62%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a suspension of 2-bromo-5-(4-t-butylphenyl)-4-hydroxy-3-methylcarbonylthiophene (1.00 g, 2.83 mmol) synthesized in Reference Synthetic Example 55 and 4-hydrazinocarbonylmethylbenzoate (550 mg, 2.83 mmol) in isopropyl alcohol (28.3 mL), tosylic acid monohydrate (146 mg, 0.85 mmol) was added, and the mixture was heated with reflux for about 1 hour. The reaction solution was concentrated, and then purified with a silica gel column chromatography (chloroform, and then chloroform/ethyl acetate=95/5) to obtain the desired product as a yellow solid (935 mg, yield 62%).

후처리

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperaturewith reflux for about 1 hour
  4. concentrationThe reaction solution was concentrated
  5. custompurified with a silica gel column chromatography (chloroform

출처 및 근거

ORD 기록
ord-bc1fe108988846048b2a5005155a412b
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07576115B2

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