1,1'-Carbonyldiimidazole → 8-(3-(Trifluoromethyl)phenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylene-3,5(4H)-dione

HRID 2050509Notes

Reaction equation

HRID 2050509 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]3[NH:12][CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>O1CCOCC1>[F:22][C:2]([F:21])([F:1])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[C:13]4[N:12]([C:23](=[O:24])[NH:20][C:18](=[O:19])[C:17]=4[CH:16]=[N:15]3)[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 27370934,5-Dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 150440768-(3-(Trifluoromethyl)phenyl)-3H,6H-1,4,5a,8a-tetraazaacenaphthylene-3,5(4H)-dioneYield 59.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred mixture of 10.0 g of 4,5-dihydro-7-(3-(trifluoromethyl)phenyl)pyrazolo(1,5-a)pyrimidine-3-carboxamide (prepared as described in Example 8) in 200 ml of dioxane at room temperature under nitrogen is added 20.0 g of 1,1'-carbonyldiimidazole. The mixture is then heated at reflux for 5 hours, and then is cooled and filtered. The filtrate is evaporated to dryness in vacuo and an excess of water is added to the residue. The white solid which forms is collected and is recrystallized from acetonitrile-ethanol to give 6.5 g of the desired product as a white solid, mp 260-262° C.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureat reflux for 5 hours
  3. temperatureis cooled
  4. filtrationfiltered
  5. customThe filtrate is evaporated to dryness in vacuo
  6. additionan excess of water is added to the residue
  7. customThe white solid which forms is collected
  8. customis recrystallized from acetonitrile-ethanol

Sources & evidence

ORD record
ord-2ae0d4fd3c004d7aa21dbdaea362f2cd
Source dataset
uspto-grants-1991_05
Patent number
US05013737

Reaction notes

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