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

HRID 2103882Notes

Reaction equation

HRID 2103882 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([C:17]([CH3:19])=O)[C:15]=2[OH:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH:20]([C:24]1[CH:33]=[C:32]([C:34]([NH:36][NH2:37])=[O:35])[CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27])[C:21]([CH3:23])=[O:22].O.S(C1C=CC(C)=CC=1)(O)(=O)=O>C(O)(C)C>[NH:20]([C:24]1[CH:33]=[C:32]([C:34]([NH:36][N:37]=[C:17]([C:14]2[C:15]([OH:16])=[C:11]([C:8]3[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=3)[S:12][CH:13]=2)[CH3:19])=[O:35])[CH:31]=[CH:30][C:25]=1[C:26]([O:28][CH3:29])=[O:27])[C:21]([CH3:23])=[O:22]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 442072892-(4-t-Butylphenyl)-3-hydroxy-4-methylcarbonylthiopheneHCID 67050072Methyl 2-acetamino-4-hydrazinocarbonylbenzoate

Product 1

HCID 86604757Methyl 2-acetamino-4-[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)carbonyl]benzoateYield 83%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 2-(4-t-butylphenyl)-3-hydroxy-4-methylcarbonylthiophene (54.8 mg, 0.2 mmol) and methyl 2-acetamino-4-hydrazinocarbonylbenzoate (50.2 mg, 0.2 mmol) in isopropyl alcohol (2 mL), tosylic acid monohydrate (11.4 mg, 0.06 mmol) was added, and the mixture was heated with reflux for 12 hours. The precipitated solid was filtered to obtain 84 mg of the desired product as a pale yellow solid (yield 83%).

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperaturewith reflux for 12 hours
  4. filtrationThe precipitated solid was filtered

Sources & evidence

ORD record
ord-102a112d4eaa4db6b42ef8c774e853e8
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Reaction notes

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