Diphenyl Ether → HCID 178469490, compound

HRID 1042977Notes

Reaction equation

HRID 1042977 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH:13][CH:14]=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16](OCC)=[O:17])[CH:10]=[CH:11][CH:12]=2)=[C:5]([CH3:26])[O:4][N:3]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:10]([C:16]([OH:17])=[C:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:14]=[N:13]3)=[CH:11][CH:12]=2)=[C:5]([CH3:26])[O:4][N:3]=1

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 57465569Diethyl ({[3-(3,5-dimethyl-4-isoxazolyl)phenyl]amino}methylidene)-propanedioate2×

Product 1

HCID 178469490HCID 178469490, compoundYield 76%

Procedure

Diethyl ({[3-(3,5-dimethyl-4-isoxazolyl)phenyl]amino}methylidene)-propanedioate (for a preparation see Intermediate 5, 75 g, 210 mmol) was suspended in boiling diphenylether (1 L) and heated to reflux for 30 minutes. The reaction mixture was cooled and precipitated with iPr2O to give the title compound as a brown powder (50 g, 76%). 1H NMR (300 MHz, DMSO-d6, ppm) δ: 12.45 (brs, 1H), 8.76 (s, 1H), 8.34 (d, J=8.6 Hz, 1H), 7.76 (s, 1H), 7.59 (d, J=8.6 Hz, 1H), 4.36 (q, J=7.1 Hz, 2H), 2.62 (s, 3H), 2.43 (s, 3H), 1.43 (s, J=7.1 Hz, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 30 minutes
  3. temperatureThe reaction mixture was cooled
  4. customprecipitated with iPr2O

Sources & evidence

ORD record
ord-18c3f4fda8cb4893bc83b38453c9b540
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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