Chloranil → HCID 13338400, compound

HRID 2417687Notes

Reaction equation

HRID 2417687 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]3[N:8]([CH2:12][CH:13]([CH3:15])[N:14]=3)[C:9]([CH3:11])=[N:10][C:5]=2[C:4]([CH3:16])=[N:3]1.C1(Cl)C(=O)C(Cl)=C(Cl)C(=O)C=1Cl>C1(C)C(C)=CC=CC=1>[CH3:1][N:2]1[C:6]2[C:7]3[N:8]([CH:12]=[C:13]([CH3:15])[N:14]=3)[C:9]([CH3:11])=[N:10][C:5]=2[C:4]([CH3:16])=[N:3]1

Participants

4

Reactant 2

HCID 8371ChloranilHCID 13338380HCID 13338380, compound

Product 1

HCID 13338400HCID 13338400, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2.4 g (0.011 mol) of 7,8-dihydro-1,3,5,8-tetramethyl-1H-imidazo[1,2-c]pyrazolo[3,4-e]pyrimidine and 5.6 g (0.022 mol) of chloranil in 400 ml of xylene is stirred under reflux four hours. The warm mixture is extracted with two 150 ml portions of 1N sodium hydroxide. The organic layer is separated, filtered, dried over MgSO4, and evaporated in vacuo. The solid residue is stirred in ether to give 1.2 g (50%) of the title compound, mp 198°-200°.

Workup

  1. temperatureunder reflux four hours
  2. extractionThe warm mixture is extracted with two 150 ml portions of 1N sodium hydroxide
  3. customThe organic layer is separated
  4. filtrationfiltered
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. stirringThe solid residue is stirred in ether

Sources & evidence

ORD record
ord-0fdd88bbdf924c38ab59a019dacce00f
Source dataset
uspto-grants-1984_09
Patent number
US04469868

Reaction notes

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