Hydrochloric Acid → HCID 13983075, compound

HRID 2291448Notes

Reaction equation

HRID 2291448 reaction equation
[CH3:1][N:2]1[C:9](=[O:10])[CH2:8][C:6](=[O:7])[N:5]([CH3:11])[C:3]1=[O:4].[Cl:12][C:13]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:14]=1[C:15](Cl)=[O:16].C(N(CC)CC)C.Cl>C(#N)C.[C-]#N.[Zn+2].[C-]#N>[Cl:12][C:13]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:14]=1[C:15]([CH:8]1[C:9](=[O:10])[N:2]([CH3:1])[C:3](=[O:4])[N:5]([CH3:11])[C:6]1=[O:7])=[O:16]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 69860Dimethylbarbituric acid

Product 1

HCID 13983075HCID 13983075, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 6342AcetonitrileSolvent

Procedure

1,3-Dimethylbarbituric acid (15.6 g, 0.1 mole), 2,4-dichlorobenzoyl chloride (20.9 g, 0.1 mole) and zinc cyanide (12.9 g, 0.11 mole) were combined in acetonitrile (175 ml). Triethylamine (10.1 g, 0.12 mole) was slowly added with cooling. The reaction mixture was then heated at reflux for one hour. After cooling, the reaction mixture was poured into 2N hydrochloric acid. The resulting product precipitate was filtered and washed with ether to afford 26.4 grams of the desired product, m.p. 123°-127° C. (80.2% yield). The structure was confirmed by instrumental analysis.

Workup

  1. temperaturewith cooling
  2. temperatureThe reaction mixture was then heated
  3. temperatureat reflux for one hour
  4. temperatureAfter cooling
  5. filtrationThe resulting product precipitate was filtered
  6. washwashed with ether

Sources & evidence

ORD record
ord-7de26c7dc21c47ad9ca1c3ada89643c8
Source dataset
uspto-grants-1989_01
Patent number
US04797147

Reaction notes

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