Ethanol → HCID 11779533, compound

HRID 465488Notes

Reaction equation

HRID 465488 reaction equation
[F:1][C:2]1[CH:14]=[C:13]([CH3:15])[C:12]2[C:11]3[C:6](=[CH:7][C:8]([F:16])=[CH:9][CH:10]=3)C(=O)[C:4]=2[CH:3]=1.[C-:18]#[N:19].[K+].[C:21](=[O:24])(O)[O-].[NH4+:25].[CH2:26]([OH:28])C>>[F:1][C:2]1[CH:14]=[C:13]([CH3:15])[C:12]2[C:11]3[C:10]([C:18]4([C:26](=[O:28])[NH:25][C:21](=[O:24])[NH:19]4)[C:4]=2[CH:3]=1)=[CH:9][C:8]([F:16])=[CH:7][CH:6]=3

Participants

5

Reactant 4

HCID 702EthanolHCID 9032Potassium CyanideHCID 14013Ammonium BicarbonateHCID 14579591HCID 14579591, compound

Product 1

HCID 11779533HCID 11779533, compound

Conditions

Temperature
125 °C

Procedure

2,7-Difluoro-4-methyl-9-fluorenone (1.3 g, 0.0056 mol), potassium cyanide (3 eq, 0.017 mol, 1.1 g), ammonium bicarbonate (3 eq, 0.017 mol, 1.3 g), and 50 mL of ethanol were placed in a sealed bomb and heated at 125° C. for 20 h. The bomb was cooled to room temperature and the contents were filtered through Celite washing with water and ethyl acetate. The filtrate was concentrated in vacuo and the residue was dissolved in 40 mL of 1N aqueous sodium hydroxide and washed with ethyl acetate (2×30 mL). The aqueous solution was acidified with concentrated hydrochloric acid and the product extracted into ethyl acetate. The organic solution was then dried and concentrated providing 1.1 g of a crude white solid which was recrystallized from ethanol to give 340 mg of 2,7-difluoro-4-methylspiro(9H-fluorene-9,4'-imidazolidine)-2',5'-dione: mp>320° C.; 1H NMR (DMSO-d6, 60 mHz) δ8.5 (s, 1H), 7.8 (m, 1H), 7.2 (m, 4H), 2.7 (s, 3H); IR (KBr) 3300, 1710, 1380, 770 cm-1 ; MS m/z 300 (M+), 229 (base peak). Analysis Calculated for C16H10F2N2O2.1/2H2O: C, 62.14; H, 3.58; N, 9.06. Found: C, 62.21; H, 3.58; N, 8.81.

Workup

  1. temperatureThe bomb was cooled to room temperature
  2. filtrationthe contents were filtered through Celite
  3. washwashing with water and ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionthe residue was dissolved in 40 mL of 1N aqueous sodium hydroxide
  6. washwashed with ethyl acetate (2×30 mL)
  7. extractionthe product extracted into ethyl acetate
  8. customThe organic solution was then dried
  9. concentrationconcentrated
  10. customproviding 1.1 g of a crude white solid which
  11. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-024873a261444b8086a2ac8b983a9848
Source dataset
uspto-grants-1992_10
Patent number
US05153211

Reaction notes

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