Hydrochloric Acid → 4-{1-[4-Acetoxy-5-(4-tert-butylphenyl)thiphen-3-yl]ethylidenehydrazinocarbonyl}-2-nitro benzoic acid

HRID 1881652Notes

Reaction equation

HRID 1881652 reaction equation
[C:1]([C:4]1[C:5]([O:19][C:20](=[O:22])[CH3:21])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][CH:10]=2)[S:7][CH:8]=1)(=O)[CH3:2].[NH:23]([C:25]([C:27]1[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[C:29]([N+:36]([O-:38])=[O:37])[CH:28]=1)=[O:26])[NH2:24].Cl.O>CN(C=O)C>[C:20]([O:19][C:5]1[C:4]([C:1](=[N:24][NH:23][C:25]([C:27]2[CH:35]=[CH:34][C:30]([C:31]([OH:33])=[O:32])=[C:29]([N+:36]([O-:38])=[O:37])[CH:28]=2)=[O:26])[CH3:2])=[CH:8][S:7][C:6]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:11][CH:10]=1)(=[O:22])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 670502974-Hydrazinocarbonyl-2-nitrobenzoic acidHCID 67050465Acetic acid 4-acetyl-2-(4-tert-butylphenyl)thiophen-3-yl ester

Product 1

HCID 578043524-{1-[4-Acetoxy-5-(4-tert-butylphenyl)thiphen-3-yl]ethylidenehydrazinocarbonyl}-2-nitro benzoic acidYield 28%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of acetic acid 4-acetyl-2-(4-tert-butylphenyl)thiophen-3-yl ester (63.3 mg, 0.2 mmol) and 4-hydrazinocarbonyl-2-nitrobenzoic acid (54.0 mg, 0.24 mmol) in DMF (1 mL) was added 12 M aqueous HCl solution (16.7 μL, 0.2 mmol). The reaction mixture was stirred overnight, and then water was added. The precipitated solid was collected by filtration and washed with water and CHCl3 to give product as a pale yellow solid (29.1 mg, yield 28%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with water and CHCl3

Sources & evidence

ORD record
ord-0b7a0ab759814431902b41cf4f15c450
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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