Hydrochloric Acid → HCID 86635888, compound

HRID 1039126Notes

Reaction equation

HRID 1039126 reaction equation
[NH:1]([C:3]([N:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH2:7][CH2:6]1)=[S:4])[NH2:2].[Cl:16][C:17]1[CH:18]=[C:19]([C:24]2[S:25][CH:26]=[C:27]([C:30]([CH3:32])=O)[C:28]=2[OH:29])[CH:20]=[CH:21][C:22]=1[Cl:23].CN(C)C=O.Cl>O>[Cl:16][C:17]1[CH:18]=[C:19]([C:24]2[S:25][CH:26]=[C:27]([C:30](=[N:2][NH:1][C:3]([N:5]3[CH2:6][CH2:7][N:8]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[CH2:9][CH2:10]3)=[S:4])[CH3:32])[C:28]=2[OH:29])[CH:20]=[CH:21][C:22]=1[Cl:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 442072882-(3,4-Dichlorophenyl)-3-hydroxy-4-(methylcarbonyl)thiopheneHCID 57957735HCID 57957735, compound

Product 1

HCID 86635888HCID 86635888, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 2-[4-hydrazinothiocarbonylpiperazin-1-yl]acetate (356 mg, 1.52 mmol) prepared in Reference Synthetic Example 10 and 2-(3,4-dichlorophenyl)-3-hydroxy-4-methylcarbonylthiophene (147 mg, 0.512 mmol) were stirred with dimethylformamide (4 mL) and concentrated hydrochloric acid (42.6 μL, 1.52 mmol) at room temperature to 60° C. for 5 days. After addition of water, the reaction mixture was filtered, and the filter cake was dried. The filter cake was mixed with chloroform and filtered, and the filtrate was concentrated then mixed with chloroform, isopropyl alcohol and n-hexane and filtered. The filter cake was dried to give the crude desired product (yield 18%). The crude product was used directly for the next reaction.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customthe filter cake was dried
  3. additionThe filter cake was mixed with chloroform
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. additionthen mixed with chloroform, isopropyl alcohol and n-hexane
  7. filtrationfiltered
  8. customThe filter cake was dried

Sources & evidence

ORD record
ord-3a6d66628a6f40f48d79b2aa4d8ac258
Source dataset
uspto-grants-2013_10
Patent number
US08552031B2

Reaction notes

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