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

HRID 1881627Notes

Reaction equation

HRID 1881627 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-6c2c5877abe346b58f80024c4d01bc89
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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