Carbon Dioxide → Cyprodinil

HRID 2106891Notes

Reaction equation

HRID 2106891 reaction equation
C(=O)(O)O.[C:5]1([NH:11][C:12]([NH2:14])=[NH:13])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:15]1([C:18](=O)[CH2:19][C:20](=O)[CH3:21])[CH2:17][CH2:16]1.C(=O)=O>C(OCC)C>[C:5]1([NH:11][C:12]2[N:14]=[C:20]([CH3:21])[CH:19]=[C:18]([CH:15]3[CH2:17][CH2:16]3)[N:13]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 110188691-Cyclopropyl-butane-1,3-dioneHCID 16217093Carbonic acid, compound with phenylguanidine (1:1)

Product 1

HCID 86367Cyprodinil

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

10 g (51 mmol) of phenylguanidine hydrogen carbonate and 9.7 g (77 mmol) of 1-cyclopropyl-1,3-butanedione are heated at 110° C. for 6 hours with stirring, the evolution of carbon dioxide which occurs subsiding as the reaction progresses. After the dark brown emulsion has been cooled to room temperature, 50 ml of diethyl ether are added and the mixture is washed twice with 20 ml of water each time, dried over sodium sulfate and filtered, and the solvent is evaporated. The dark brown oil which remains (=13.1 g) is purified by column chromatography over silica gel (diethyl ether/toluene: 5/3). After the eluant mixture has been evaporated off, the brown oil is made to crystallise and recrystallised from diethyl ether/petroleum ether at 30°-50° C. Light-brown crystals are obtained. Melting point: 67°-69° C.; yield: 8.55 g (38 mmol) (=74.5% of the theoretical yield).

Workup

  1. customas the reaction progresses
  2. washthe mixture is washed twice with 20 ml of water each time
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customthe solvent is evaporated
  6. customis purified by column chromatography over silica gel (diethyl ether/toluene: 5/3)
  7. customAfter the eluant mixture has been evaporated off
  8. customto crystallise
  9. customrecrystallised from diethyl ether/petroleum ether at 30°-50° C
  10. customLight-brown crystals are obtained
  11. customyield: 8.55 g (38 mmol) (=74.5% of the theoretical yield)

Sources & evidence

ORD record
ord-f7a050a9cc624e9596e63134d9ac88a5
Source dataset
uspto-grants-1990_06
Patent number
US04931560

Reaction notes

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