Hydrochloric Acid → HCID 73043918, compound

HRID 1039123Notes

Reaction equation

HRID 1039123 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2[S:15][CH:16]=[C:17]([C:20]([CH3:22])=O)[C:18]=2[OH:19])[CH:10]=[CH:11][C:12]=1[Cl:13].[NH:23]([C:25]([N:27]1[CH2:32][CH2:31][CH:30]([C:33]([O:35][CH3:36])=[O:34])[CH2:29][CH2:28]1)=[S:26])[NH2:24].Cl>O>[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2[S:15][CH:16]=[C:17]([C:20](=[N:24][NH:23][C:25]([N:27]3[CH2:32][CH2:31][CH:30]([C:33]([O:35][CH3:36])=[O:34])[CH2:29][CH2:28]3)=[S:26])[CH3:22])[C:18]=2[OH:19])[CH:10]=[CH:11][C:12]=1[Cl:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24855846Methyl 1-hydrazinothiocarbonylpiperidine-4-carboxylateHCID 442072882-(3,4-Dichlorophenyl)-3-hydroxy-4-(methylcarbonyl)thiophene

Product 1

HCID 73043918HCID 73043918, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethylformamide solution (600 μL) of 2-(3,4-dichlorophenyl)-3-hydroxy-4-methylcarbonylthiophene (30 mg, 0.10 mmol) and methyl 1-hydrazinothiocarbonyl-piperidine-4-carboxylate (46 mg, 0.20 mmol) prepared in Reference Synthetic Example 2, concentrated hydrochloric acid (9 μL, 0.1 mmol) was added at room temperature, and the resulting solution was stirred at room temperature for 8 hours, then mixed with water and extracted with ethyl acetate. The extract was washed with 1 M hydrochloric acid and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1) and recrystallized from chloroform to give the desired product (yield 55%).

Workup

  1. additionwas added at room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with 1 M hydrochloric acid and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1)
  7. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-21fc972d3c6f4b769d9fbd6de7581106
Source dataset
uspto-grants-2013_10
Patent number
US08552031B2

Reaction notes

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