Dimethylformamide → HCID 72360122, compound

HRID 1881638Notes

Reaction equation

HRID 1881638 reaction equation
CN(C)C=O.[C:6]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:17][CH:18]=[C:19]([C:22]([CH3:24])=O)[C:20]=2[OH:21])=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].[NH:25]([C:27]([NH:29][C:30]1[S:34][C:33]([C:35]([O:37][CH3:38])=[O:36])=[CH:32][CH:31]=1)=[S:28])[NH2:26]>Cl.O>[C:6]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[S:17][CH:18]=[C:19]([C:22](=[N:26][NH:25][C:27]([NH:29][C:30]3[S:34][C:33]([C:35]([O:37][CH3:38])=[O:36])=[CH:32][CH:31]=3)=[S:28])[CH3:24])[C:20]=2[OH:21])=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 442072892-(4-t-Butylphenyl)-3-hydroxy-4-methylcarbonylthiopheneHCID 86604759HCID 86604759, compound

Product 1

HCID 72360122HCID 72360122, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

Dimethylformamide (1.3 ml) and conc. hydrochloric acid (1 drop) were added to 2-(4-t-butylphenyl)-3-hydroxy-4-methylcarbonylthiophene (70 mg, 0.26 mmol) synthesized in Reference Synthetic Example 33 and methyl 5-hydrazinocarbonothioylamino-2-thiophenecarboxylate (59 mg, 0.26 mmol) synthesized in Reference Synthetic Example 57, and the mixture was stirred overnight at room temperature. Water was added, and the precipitated solid was filtered. The obtained solid was extracted with chloroform, dried over anhydrous sodium sulfate. The organic layer was concentrated, and purified with a silica gel column chromatography (chloroform/methanol=95/5) to obtain the desired product as a pale yellow solid (112 mg, yield 90%).

Workup

  1. customsynthesized in Reference Synthetic Example 57
  2. filtrationthe precipitated solid was filtered
  3. extractionThe obtained solid was extracted with chloroform
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe organic layer was concentrated
  6. custompurified with a silica gel column chromatography (chloroform/methanol=95/5)

Sources & evidence

ORD record
ord-79c577963c484d1a924a2c52d8eeda53
Source dataset
uspto-grants-2012_11
Patent number
US08318796B2

Reaction notes

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