Dimethyl Sulfoxide → HCID 131718401, compound

HRID 1033147Notes

Reaction equation

HRID 1033147 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)([O-])=[O:2].[CH3:13]S(C)=O.[H][H].C(N(CC)C1C=CC(C=O)=CC=1)C>[Pt].CO.C(O)(=O)C>[C:8]([C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:2])=[CH2:13])=[CH:5][CH:6]=1)([OH:10])=[O:9]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 61084-Nitrobenzoic Acid2×HCID 671144-(Diethylamino)benzaldehydeHCID 178418361HCID 178418361, compound2×

Product 1

HCID 131718401HCID 131718401, compound

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

122.2 g (731 mmols) of p-nitrobenzoic acid, 11.3 g of dimethylsulfoxide, 2.0 g of a 5% platinum-supported catalyst, and 260 g of methanol were charged into a one liter autoclave, followed by filling hydrogen at a pressure of about 4 kg/cm2 and continuing agitation at room temperature until an equivalent of hydrogen was reacted with p-nitrobenzoic acid. After removal of the catalyst, 120.0 g (677 mmols) of 4-diethylaminobenzaldehyde, 30.0 g of acetic acid and 100 g of methanol were added to the resultant residue, followed by agitation at room temperature for 5 hours. After removal of the resultant crystals by filtration, they were washed with methanol to obtain yellow crystals and dried to isolate 187.6 g (yield 88.7%) of α-p-(diethylamino)phenyl]-N-(4-carboxyphenyl)nitrone with a purity of 96%. The thus obtained α-[p-(diethylamino)-phenyl]-N-(4-carboxyphenyl)nitrone had the following results with respect to mass spectra (MS), NMR spectra (NMR), IR spectra (IR) and elementary analysis.

Workup

  1. additionwere charged into a one liter autoclave
  2. customat room temperature
  3. customAfter removal of the resultant crystals
  4. filtrationby filtration, they
  5. washwere washed with methanol
  6. customto obtain yellow crystals
  7. customdried

Sources & evidence

ORD record
ord-ef5ea3eeb4b9441a8e8b01ed1a36bfc0
Source dataset
uspto-grants-1994_05
Patent number
US05310620

Reaction notes

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