Acetic Acid → 5-[(5-bromothiophen-2-yl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dione

HRID 2305400Notes

Reaction equation

HRID 2305400 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[N:5]=[C:4]([SH:9])[N:3]=1.[Br:10][C:11]1[S:15][C:14]([CH:16]=O)=[CH:13][CH:12]=1.C(O)(=O)C.CN(C=O)C>O>[Br:10][C:11]1[S:15][C:14]([CH:16]=[C:7]2[C:6](=[O:8])[NH:5][C:4](=[S:9])[NH:3][C:2]2=[O:1])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6228DimethylformamideHCID 784285-Bromothiophene-2-carbaldehydeHCID 178516656HCID 178516656, compound

Product 1

HCID 9460905-[(5-bromothiophen-2-yl)methylidene]-2-sulfanylidene-1,3-diazinane-4,6-dioneYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a procedure identical to Example 1, 0.144 g (1 mmol) of 4,6-dihydroxy-2-mercaptopyrimidine, and 0.207 g (1 mmol) of 5-bromothiophenecarboxaldehyde in a solution of 2 ml of glacial acetic acid and 4 ml of DMF was heated at 80° C. for 12 hours. Upon cooling to room temperature, the reaction was poured into water and the precipitate collected by filtration. The crude product was washed with water, and the solid boiled in methanol for 1 minute. Filtration provided 92 mg of product as an orange solid.

Workup

  1. filtrationthe precipitate collected by filtration
  2. washThe crude product was washed with water
  3. filtrationFiltration

Sources & evidence

ORD record
ord-6c6ff80b61f04dd1af0652e3ecf5c57e
Source dataset
uspto-grants-2002_08
Patent number
US06440985B1

Reaction notes

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