Diethyl (ethoxymethylene)malonate → Diethyl ({[3-(3,5-dimethyl-4-isoxazolyl)phenyl]amino}methylidene)-propanedioate

HRID 1042976Notes

Reaction equation

HRID 1042976 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([CH:11]=[CH:12][CH:13]=2)[NH2:10])=[C:5]([CH3:14])[O:4][N:3]=1.C(O[CH:18]=[C:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])C>>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH:10][CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:11]=[CH:12][CH:13]=2)=[C:5]([CH3:14])[O:4][N:3]=1

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 116870263-(3,5-Dimethyl-isoxazol-4-yl)-phenylamine2×

Product 1

HCID 57465569Diethyl ({[3-(3,5-dimethyl-4-isoxazolyl)phenyl]amino}methylidene)-propanedioateYield 52%

Conditions

Temperature
130 °C

Procedure

3-(3,5-Dimethyl-4-isoxazolyl)aniline (for a preparation see Intermediate 2, 80 g, 420 mmol) and diethyl ethoxymethylenemalonate (92 g, 425 mmol) were mixed together and heated to 130° C. for 20 minutes, liberating ethanol, which was evaporated under reduced pressure. The reaction mixture was poured into iPr2O (1 L) and the resulted precipitate filtered off and washed with iPr2O. The resulting solid was recrystallised from acetonitrile to give the title compound as a brown solid (78 g, 52%).

Workup

  1. additionwere mixed together
  2. customliberating ethanol, which was evaporated under reduced pressure
  3. additionThe reaction mixture was poured into iPr2O (1 L)
  4. filtrationthe resulted precipitate filtered off
  5. washwashed with iPr2O
  6. customThe resulting solid was recrystallised from acetonitrile

Sources & evidence

ORD record
ord-8868b3cf06764fb18fba31226de5ad0b
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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