Dimethylformamide dimethyl acetal → HCID 28887991, compound

HRID 1988806Notes

Reaction equation

HRID 1988806 reaction equation
[C:1]1([NH:11][C:12](=[S:15])[NH:13][NH2:14])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:16]OC(OC)N(C)C>O1CCOCC1>[C:1]1([N:11]2[CH:16]=[N:14][NH:13][C:12]2=[S:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 2760175N-(Naphthalen-1-yl)hydrazinecarbothioamide

Product 1

HCID 28887991HCID 28887991, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-(1-naphthalenyl)-3-thiosemicarbazide (4.01 g, 18.4 mmol) and N,N,-dimethylformamide dimethyl acetal (2.50 mL, 18.8 mmol) in 1,4-dioxane (40 mL) was stirred at room temperature for 16 h. The mixture was concentrated under reduced pressure. The residue was taken in hexane and Et2O and the solution was stirred until a suspension was obtained. The suspension was filtered and the solid was triturated with hexane:Et2O (4:1), then was dried under reduced pressure to give the title compound (4.19 g, 90% yield) as a beige solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customwas obtained
  3. filtrationThe suspension was filtered
  4. customthe solid was triturated with hexane:Et2O (4:1)
  5. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-c1ae9541110a4cd5b3bc31d9aa5cfb60
Source dataset
uspto-grants-2010_01
Patent number
US07642277B2

Reaction notes

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