Triethylamine → 3-Cyclopentyloxy-4-methoxybenzal hydantoin

HRID 1067388Notes

Reaction equation

HRID 1067388 reaction equation
CCOP(OCC)([CH:6]1[NH:12][C:10](=[O:11])[NH:9][C:7]1=[O:8])=O.C(N(CC)CC)C.[CH:23]1([O:28][C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][C:36]=2[O:37][CH3:38])[CH:32]=O)[CH2:27][CH2:26][CH2:25][CH2:24]1>C(#N)C>[CH:23]1([O:28][C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][C:36]=2[O:37][CH3:38])[CH:32]=[C:6]2[NH:12][C:10](=[O:11])[NH:9][C:7]2=[O:8])[CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 3516088Diethyl 5-hydantoylphosphonate

Product 1

HCID 543507273-Cyclopentyloxy-4-methoxybenzal hydantoinYield 77.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of diethyl 5-hydantoylphosphonate (10 g, 42.3 mmol) and triethylamine (5.70 g, 56 mmol), in dry acetonitrile (100 ml), at room temperature was added a solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (8 g, 36.3 mmol) in dry acetonitrile (75 ml), dropwise over 30 minutes. The resulting mixture was stirred at room temperature overnight, after which volatiles were removed in vacuo. The residue was diluted with 0.05N HCl (120 ml) and the precipitate collected by filtration. Recrystallization of this material with methylene chloride/methanol/diethyl ether afforded the title compound as a pale yellow solid (8.54 g), m.p. 220-222° C.

Workup

  1. customafter which volatiles were removed in vacuo
  2. additionThe residue was diluted with 0.05N HCl (120 ml)
  3. filtrationthe precipitate collected by filtration
  4. customRecrystallization of this material with methylene chloride/methanol/diethyl ether

Sources & evidence

ORD record
ord-45b0bca773284945b314b1cf571bdcad
Source dataset
uspto-grants-2001_06
Patent number
US06248769B1

Reaction notes

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