Hydrochloric Acid → 4-[2,5-Dioxo-4-hydroxymethyl-4-phenylimidazolidin-1-yl]-2-methoxybenzonitrile

HRID 389906Notes

Reaction equation

HRID 389906 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[O:11])=[CH:5][C:4]=1[O:12][CH3:13])#[N:2].[OH:14][CH2:15][C:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:18](O)=[O:19])[NH2:17].[Na].Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1.O>[O:11]=[C:10]1[NH:17][C:16]([CH2:18][OH:19])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15](=[O:14])[N:9]1[C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[C:4]([O:12][CH3:13])[CH:5]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 2328882-Amino-3-hydroxy-2-phenylpropanoic acidHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 148478564-Isocyanato-2-methoxybenzonitrile

Product 1

HCID 671311834-[2,5-Dioxo-4-hydroxymethyl-4-phenylimidazolidin-1-yl]-2-methoxybenzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 384 mg of 4-cyano-3-methoxyphenyl isocyanate (prepared according to WO 2007/137874) in 8 mL dioxane is added to a solution of 200 mg of 2-hydroxymethyl-2-phenylglycine (prepared according to literature procedure) in an aqueous solution of 1.8 mL 1N sodium hydroxyde in 2 mL of water. The mixture is stirred at room temperature overnight, acidified by adding 3 mL 12N HCl and heated at 110° C. for 2 hours. The solution is then treated with a saturated aqueous solution of sodium bicarbonate, extracted with ethyl acetate, dried over sulfate magnesium, filtered, evaporated and purified over silica gel while eluting with 60/40 heptane/ethyl acetate mixture to give the expected product.

Workup

  1. temperatureheated at 110° C. for 2 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sulfate magnesium
  4. filtrationfiltered
  5. customevaporated
  6. custompurified over silica gel
  7. washwhile eluting with 60/40 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-787d9ef3766941ca8c903b3a24196dc7
Source dataset
uspto-grants-2013_02
Patent number
US08383608B2

Reaction notes

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