Methanol → N-(5-Nitro-2-methoxyphenyl)-2,2,5-trimethyl-beta-oxo-1,3-dioxane-5-propanamide

HRID 989592Notes

Reaction equation

HRID 989592 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:4]=1[NH2:5].[CH3:13][C:14]1([CH3:28])[O:19][CH2:18][C:17]([CH3:27])([C:20](=[O:26])[CH2:21][C:22](OC)=[O:23])[CH2:16][O:15]1.C1(C)C=CC=C(C)C=1.CO>CCCCCCCC>[N+:10]([C:7]1[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[C:4]([NH:5][C:22](=[O:23])[CH2:21][C:20](=[O:26])[C:17]2([CH3:27])[CH2:16][O:15][C:14]([CH3:13])([CH3:28])[O:19][CH2:18]2)[CH:6]=1)([O-:12])=[O:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 74472-Methoxy-5-nitroanilineHCID 7929M-XyleneHCID 53655320HCID 53655320, compound

Product 1

HCID 19895265N-(5-Nitro-2-methoxyphenyl)-2,2,5-trimethyl-beta-oxo-1,3-dioxane-5-propanamide

Reagents, catalysts & solvents 1

HCID 356OctaneSolvent

Procedure

2Methoxy-5-nitroaniline (63.06 g, 0.375 mol) and methyl 2,2,5-trimethyl-b-oxo-1,3-dioxane-5-propanoate (90.0 g, 0.391 mol) were dispersed in n-octane (500 mL) and m-xylene (100 mL) in a 2-liter three-necked flask. The mixture was heated at the boiling point while methanol was continuously removed by a very slow nitrogen sweep. After 2 hr of heating the solution was allowed to cool slowly with good stirring; the yellow-orange precipitate which formed was filtered and allowed to air dry. The crude precipitate was dissolved in ethyl ether and extracted with dilute hydrochloric acid, after which the ethereal solution was washed once with dilute sodium bicarbonate, once with water, the organic and aqueous layers separated, and the organic layer dried over magnesium sulfate. The mixture was filtered and the excess solvent removed in vacuo. The residue was recrystallized from ethyl alcohol, m.p. 113-5° C.; H-NMR was consistent. Elemental analysis calculated for C17H22N5O7: C, 55.73; H, 6.05; N, 7.65. Found: C, 55.64; H. 6.14; N, 7.53.

Workup

  1. customwas continuously removed by a very slow nitrogen sweep
  2. temperatureAfter 2 hr of heating the solution
  3. temperatureto cool slowly with good stirring
  4. customthe yellow-orange precipitate which formed
  5. filtrationwas filtered
  6. customto air dry
  7. dissolutionThe crude precipitate was dissolved in ethyl ether
  8. extractionextracted with dilute hydrochloric acid
  9. washafter which the ethereal solution was washed once with dilute sodium bicarbonate, once with water
  10. customthe organic and aqueous layers separated
  11. dry with materialthe organic layer dried over magnesium sulfate
  12. filtrationThe mixture was filtered
  13. customthe excess solvent removed in vacuo
  14. customThe residue was recrystallized from ethyl alcohol, m.p. 113-5° C.

Sources & evidence

ORD record
ord-e37d5261a0a24af69b8ff5a4c9b992ae
Source dataset
uspto-grants-2002_10
Patent number
US06458521B1

Reaction notes

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