Sodium → HCID 54536020, compound

HRID 867473Notes

Reaction equation

HRID 867473 reaction equation
[Na].[CH3:2][N:3]1[CH:7](P(OCC)(=O)OCC)[C:6](=[O:16])[NH:5][C:4]1=[O:17].[CH:18]1([N:24]([CH3:42])[C:25](=[O:41])[CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[C:32]([CH:39]=O)[CH:31]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)C>[CH:18]1([N:24]([CH3:42])[C:25](=[O:41])[CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[C:32]([CH:39]=[C:7]3[N:3]([CH3:2])[C:4](=[O:17])[NH:5][C:6]3=[O:16])[CH:31]=2)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 13364983HCID 13364983, compoundHCID 13937024Diethyl (3-methyl-2,5-dioxoimidazolidin-4-yl)phosphonate

Product 1

HCID 54536020HCID 54536020, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (0.079 g, 0.003 g atom) was dissolved in ethanol (20 mL) and diethyl 1-methyl-2,4-dioxoimidazolidine-5-phosphonate (0.86 g, 3.4 mmol) added. After 5 minutes, N-cyclohexyl-4-(3-formyl-4-nitrophenoxy)-N-methylbutanamide (1 g, 2.9 mmol) was added and the mixture stirred at room temperature for 90 minutes. The solvent was evaporated and the residue diluted with water and extracted with dichloromethane to give a foam. Crystallization from hexane/dichloromethane afforded N-cyclohexyl-N-methyl-4-[3-[(1-methyl-2,4-dioxoimidazolidin-5-ylidene)methyl]-4-nitrophenoxy]butanamide (0.96 g, 75%) as a 3:1 mixture of geometrical isomers, m.p. 149°-154° C.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue diluted with water
  3. extractionextracted with dichloromethane
  4. customto give a foam
  5. customCrystallization from hexane/dichloromethane

Sources & evidence

ORD record
ord-c777c8a6690f47f2a8e16f0dabe9e8f9
Source dataset
uspto-grants-1988_10
Patent number
US04775674

Reaction notes

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