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

HRID 892403
Notes
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Reaction equation

HRID 892403 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.CO>CCCCCCCC.C1(C)C=CC=C(C)C=1.C(OCC)C>[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 887MethanolHCID 74472-Methoxy-5-nitroanilineHCID 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 3

HCID 356OctaneSolvent
HCID 3283
Diethyl Ether
Solvent
HCID 7929M-XyleneSolvent

Procedure

2-Methoxy-5-nitroaniline (63 parts) and methyl 2,2,5-trimethyl-β-oxo-1,3-dioxane-5-propanoate (90 parts) are dispersed in n-octane (500 parts) and m-xylene (100 parts). The mixture is stirred vigorously while methanol is removed by a slow distillation under an inert atmosphere. Additional m-xylene is added as needed to replenish the reaction solvent as it co-distills with methanol of reaction. After the solution is allowed to cool slowly with vigorous stirring, a yellow-orange solid resulted, ca. 2 hr. The precipitate is dissolved in ethyl ether and the ethereal solution extracted with dilute hydrochloric acid, washed once with dilute sodium bicarbonate, once with water, the organic layer separated from the aqueous layer, dried and the excess solvent removed in vacuo. The residue is recrystallized from ethyl alcohol, m.p. 113-115° C. Proton NMR and combustion analysis were consistent with those values predicted for the desired product. Combustion Analysis for C17H22N2O7 --Calculated: C, 55.7%; H, 6.1%; N, 7.7%. Found: C, 55.6%; H, 6.1%; N, 7.5%.

Workup

  1. customis removed by a slow distillation under an inert atmosphere
  2. additionAdditional m-xylene is added
  3. customco-distills with methanol of reaction
  4. temperatureto cool slowly with vigorous stirring
  5. customa yellow-orange solid resulted, ca. 2 hr
  6. extractionthe ethereal solution extracted with dilute hydrochloric acid
  7. washwashed once with dilute sodium bicarbonate, once with water
  8. customthe organic layer separated from the aqueous layer
  9. customdried
  10. customthe excess solvent removed in vacuo
  11. customThe residue is recrystallized from ethyl alcohol, m.p. 113-115° C

Sources & evidence

ORD record
ord-01ab68503cb142bb91fc4dae038e4d49
Source dataset
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05118599

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes