Hydrochloric Acid → Dimethyl 2,3-dianilinobut-2-enedioate

HRID 638679Notes

Reaction equation

HRID 638679 reaction equation
O/[C:2](/[C:9]([O:11][CH3:12])=[O:10])=[C:3](/O)\[C:4]([O:6][CH3:7])=[O:5].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>CO>[CH3:7][O:6][C:4](=[O:5])[C:3]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:2]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 54699194Dihydroxyfumaric acid dimethyl ester

Product 1

HCID 68545930Dimethyl 2,3-dianilinobut-2-enedioateYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a round bottom flask with a teflon stirbar, 25 g (142 mmol) of dimethyl dihydroxyfumarate (prepared according to a procedure described in U.S. Pat. No. 3,334,102), 29.0 g (312.5 mmol) of aniline, 0.1 mL of concentrated HCl, and 90 mL of methyl alcohol were mixed and heated to reflux for 3 hours. The reaction mixture was cooled to room temperature and left overnight in a refrigerator. The next morning, the resulting thick paste was filtered on a coarse frit, washed with a 50% (v:v) methanol-water mixture, and dried in a vacuum oven, yielding 30.1 g (65% yield) which, according to NMR analysis, was a mixture of E/Z isomers (E:Z˜1:2).

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. filtrationThe next morning, the resulting thick paste was filtered on a coarse frit
  4. washwashed with a 50% (v:v) methanol-water mixture
  5. customdried in a vacuum oven
  6. customyielding 30.1 g (65% yield) which
  7. additiona mixture of E/Z isomers (E:Z˜1:2)

Sources & evidence

ORD record
ord-6420ab5bab00442f86a5a1a530b110e4
Source dataset
uspto-grants-2010_04
Patent number
US07691197B2

Reaction notes

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