Methyl iodide → HCID 69848741, compound

HRID 1459394Notes

Reaction equation

HRID 1459394 reaction equation
N1C=CC=CC=1C[C:8]1(CC2C=CC=CN=2)[N:12]([C:13]23[CH2:22][CH:17]4[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]4)[CH2:14]2)[CH2:20]3)[C:11](=S)[NH:10][C:9]1=[O:24].C(=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[C:13]12([N:12]3[CH2:8][C:9](=[O:24])[N:10]=[CH:11]3)[CH2:20][CH:19]3[CH2:21][CH:15]([CH2:16][CH:17]([CH2:18]3)[CH2:22]1)[CH2:14]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 131721042HCID 131721042, compound

Product 1

HCID 69848741HCID 69848741, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under a N2 atmosphere in 50 ml of acetone were combined 0.432 g (1 mmol) of bispyridylmethyl N-1-adamantyl thiohydantoin, 0.138 g (1 mmol) of potassium carbonate and 0.142 g (1 mmol) of methyl iodide and the reaction mixture was allowed to stir at room temperature for 48 hours. The reaction mixture was concentrated in vacuo and partitioned in 100 ml EtOAc/10 ml H2O. The organic layer was separated, washed with H2 O(4×10 ml), brine (1x), dried over NaSO4 and concentrated in vacuo. The crude product was purified via column chromatography (silica gel: 92.5/7.25 EtOAc/MeOH) and crystallized from isopropyl ether/hexane (IPE/Hex) to yield N-1-adamantylimidazolinone

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned in 100 ml EtOAc/10 ml H2O
  3. customThe organic layer was separated
  4. washwashed with H2 O(4×10 ml), brine (1x)
  5. dry with materialdried over NaSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified via column chromatography (silica gel: 92.5/7.25 EtOAc/MeOH)
  8. customcrystallized from isopropyl ether/hexane (IPE/Hex)

Sources & evidence

ORD record
ord-dc9f0ba1b5a140e6a2eed761c52d9a1d
Source dataset
uspto-grants-1998_12
Patent number
US05854232

Reaction notes

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