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4-Methoxybenzohydrazide → Ethyl 6-{2-[2-(4-methoxybenzoyl)hydrazino]-2-oxoethyl}-1-benzothiophene-2-carboxylate

HRID 500668
Notes
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Reaction equation

HRID 500668 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]2[CH:14]=[C:13]([CH2:15][C:16]([OH:18])=O)[CH:12]=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2].[CH3:19][O:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([NH:27][NH2:28])=[O:26])=[CH:23][CH:22]=1.[Cl-].C(N=C=NCCC[NH+](C)C)C>CN(C=O)C>[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([NH:27][NH:28][C:16](=[O:18])[CH2:15][C:13]2[CH:12]=[CH:11][C:9]3[CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[S:7][C:8]=3[CH:14]=2)=[O:26])=[CH:29][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 767924-MethoxybenzohydrazideHCID 53519323-(Ethyliminomethylideneamino)propyl-dimethylazanium chlorideHCID 59424238[2-(Ethoxycarbonyl)-1-benzothien-6-yl]acetic acid

Product 1

HCID 59424237Ethyl 6-{2-[2-(4-methoxybenzoyl)hydrazino]-2-oxoethyl}-1-benzothiophene-2-carboxylateYield 49.8%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

To a solution of [2-(ethoxycarbonyl)-1-benzothien-6-yl]acetic acid (100 mg, 0.38 mmol) and 4-methoxybenzohydrazide (63 mg, 0.38 mmol) in 2 mL DMF was added 3-{[(ethylimino)methylene]amino}-N,N-dimethylpropane-1-aminium chloride (91 mg, 0.47 mmol). The reaction was stirred at ambient temperature for 12 hours. The reaction mixture was loaded directly onto a reverse phase C18 column for purification to give 78 mg (49%) of the title compound as a white solid. LC/MS (EI): cal'd 413.1 (MH+), exp 413.1 (MH+).

Workup

  1. customThe reaction mixture was loaded directly onto a reverse phase C18 column for purification

Sources & evidence

ORD record
ord-615a74f836c34a0680e557166989e297
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07772238B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes