Hydrochloric Acid → HCID 57554771, compound

HRID 1511897Notes

Reaction equation

HRID 1511897 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[O:19][CH2:18][C:17](=O)[CH2:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:21](=[O:24])([O-])[O-].[NH4+:25].[NH4+:26].[C-]#N.[K+].Cl.C#N.[CH2:33]([OH:35])C>O>[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:16][C:17]3([NH:26][C:33](=[O:35])[NH:25][C:21]3=[O:24])[CH2:18][O:19]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 702EthanolHCID 768Hydrogen CyanideHCID 9032Potassium CyanideHCID 517111Ammonium CarbonateHCID 57554643HCID 57554643, compound

Product 1

HCID 57554771HCID 57554771, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5-(4-octylphenyl)dihydrofuran-3(2H)-one (0.8 g, 2.92 mmol) and ammonium carbonate (1.037 g, 13.12 mmol) (Aldrich) were combined in ethanol (12.05 ml) and water (12.05 ml). Potassium cyanide (0.209 g, 3.21 mmol) (Fluka) was added and the reaction heated at about 80° C. for about 16 h. Cool the reaction and add concentrated HCl until acidic (caution for HCN gas formation). The precipitate was collected by vacuum filtration and washed with water. It was suspended in methylene chloride, filtered, and washed with methylene chloride to provide 8-(4-octylphenyl)-7-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione (0.545 g, 1.582 mmol, 54.3% yield) as a white solid:

Workup

  1. temperatureCool
  2. customthe reaction
  3. filtrationThe precipitate was collected by vacuum filtration
  4. washwashed with water
  5. filtrationfiltered
  6. washwashed with methylene chloride

Sources & evidence

ORD record
ord-4b64a9c67fe1476bb3ca1adb149709a4
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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