Hydrochloric Acid → HCID 72360022, compound

HRID 1881637Notes

Reaction equation

HRID 1881637 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][CH:14]=[C:13]([C:16](=[N:18][NH:19][C:20]([NH:22][C:23]3[CH:32]=[CH:31][C:26]([C:27]([O:29]C)=[O:28])=[C:25]([N+:33]([O-:35])=[O:34])[CH:24]=3)=[S:21])[CH3:17])[C:12]=2[OH:36])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl.O>C(O)(C)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:15][CH:14]=[C:13]([C:16](=[N:18][NH:19][C:20]([NH:22][C:23]3[CH:32]=[CH:31][C:26]([C:27]([OH:29])=[O:28])=[C:25]([N+:33]([O-:35])=[O:34])[CH:24]=3)=[S:21])[CH3:17])[C:12]=2[OH:36])=[CH:7][CH:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 72360032Methyl 4-{[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)carbonothioyl]amino}-2-nitrobenzoate

Product 1

HCID 72360022HCID 72360022, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Methyl 4-{[(2-{1-[5-(4-t-butylphenyl)-4-hydroxy-3-thienyl]ethylidene}hydrazino)carbonothioyl]amino}-2-nitrobenzoate (95 mg, 0.18 mmol) synthesized in Synthetic Example 92 was dissolved in isopropyl alcohol (1.8 mL), and 0.2 M sodium hydroxide aqueous solution (2.0 mL, 0.40 mmol) was added thereto, followed by stirring overnight at room temperature. After completion of the stirring, 1 M hydrochloric acid (0.40 mL, 0.40 mmol) and water were added thereto, and the precipitated solid was filtered to obtain 57 mg of the desired product as a pale yellow solid (yield 61%).

Workup

  1. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-09d983f9705b4ba1ab4191e813ff12e1
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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