2-(4-t-Butylphenyl)-3-hydroxy-4-methylcarbonylthiophene → HCID 72360032, compound

HRID 2103904

Reaction equation

HRID 2103904 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:22]([NH:24][C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[C:27]([N+:35]([O-:37])=[O:36])[CH:26]=1)=[S:23])[NH2:21]>Cl.CN(C)C=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[C:14]([C:17](=[N:21][NH:20][C:22]([NH:24][C:25]3[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[C:27]([N+:35]([O-:37])=[O:36])[CH:26]=3)=[S:23])[CH3:19])[C:15]=2[OH:16])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 442072892-(4-t-Butylphenyl)-3-hydroxy-4-methylcarbonylthiopheneHCID 86014590Methyl 4-hydrazinocarbonothioylamino-2-nitrobenzoate

Product 1

HCID 72360032HCID 72360032, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 6228DimethylformamideSolvent

Procedure

Dimethylformamide (1.3 mL) and conc. hydrochloric acid (1 drop) were added to 2-(4-t-butylphenyl)-3-hydroxy-4-methylcarbonylthiophene (71 mg, 0.26 mmol) synthesized in Reference Synthetic Example 33 and methyl 4-hydrazinocarbonothioylamino-2-nitrobenzoate (70 mg, 0.26 mmol) synthesized in Reference Synthetic Example 56, and the mixture was stirred at room temperature for 2 days. The precipitated solid was filtered to obtain 110 mg of the desired product as a pale yellow solid (yield 81%).

Workup

  1. customsynthesized in Reference Synthetic Example 56
  2. filtrationThe precipitated solid was filtered

Sources & evidence

ORD record
ord-d3e90faf332f4b37b52bee71ddf65a1d
Source dataset
uspto-grants-2009_08
Patent number
US07576115B2

Linked notes

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