Methanol → HCID 20498189, compound

HRID 2309104Notes

Reaction equation

HRID 2309104 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1C1NC(=O)NC1=O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].O.[C:25](=[O:28])([O-])[O-:26].[NH4+:29].[NH4+].[CH3:31]O>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[NH:29][CH2:31][C:25]([OH:26])=[O:28]

Participants

6

Reactant 5

HCID 887MethanolHCID 962WaterHCID 2260675-(furan-2-yl)imidazolidine-2,4-dioneHCID 517111Ammonium CarbonateHCID 17749109Barium hydroxide, octahydrate

Product 1

HCID 20498189HCID 20498189, compoundYield 52%

Procedure

The 5-(2-furyl)-hydantoin from Step A (22.0 g, 0.133 mol) and barium hydroxide octahydrate (67.3 g, 0.213 mol) were added to 325 ml of boiling water. The mixture was refluxed for 24 hrs., cooled to room temperature, and then the barium carbonate was filtered off. The filtrate was treated again with ammonium carbonate (12.8 g, 0.133 mol) to precipitate the barium remaining in solution. The resulting mixture was refluxed for 5 minutes and filtered. The filtrate was evaporated to dryness. The remaining brown crystals were recrystallized from a 1:2 mixture of water:methanol to give 9.7 g (52% yield) of 2-furylglycine as light beige crystals: mp 195°-199° C.

Workup

  1. temperatureThe mixture was refluxed for 24 hrs
  2. filtrationthe barium carbonate was filtered off
  3. customto precipitate the barium remaining in solution
  4. temperatureThe resulting mixture was refluxed for 5 minutes
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customThe remaining brown crystals were recrystallized from a 1:2 mixture of water

Sources & evidence

ORD record
ord-3594dd8c731b4b9c9f6abbae35cf9500
Source dataset
uspto-grants-1987_09
Patent number
US04692512

Reaction notes

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