Diethyl (ethoxymethylene)malonate → Diethyl 2-(((3-(3,5-dimethylisoxazol-4-yl)-4-methoxyphenyl)amino)methylene)malonate

HRID 1042995Notes

Reaction equation

HRID 1042995 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH2:15])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])=[C:5]([CH3:16])[O:4][N:3]=1.C(O[CH:20]=[C:21]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:22]([O:24][CH2:25][CH3:26])=[O:23])C>>[CH3:1][C:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH:15][CH:20]=[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])=[C:5]([CH3:16])[O:4][N:3]=1

Participants

3

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 57465571[3-(3,5-Dimethyl-4-isoxazolyl)-4-(methyloxy)phenyl]amine

Product 1

HCID 57465590Diethyl 2-(((3-(3,5-dimethylisoxazol-4-yl)-4-methoxyphenyl)amino)methylene)malonate

Conditions

Temperature
130 °C

Procedure

[3-(3,5-Dimethyl-4-isoxazolyl)-4-(methyloxy)phenyl]amine (for a preparation see Intermediate 60, 27.4 g, 126 mmol) was dissolved in diethyl [(ethyloxy)methylidene]propanedioate (27.1 g, 126 mmol) and heated to 130° C. The solution was heated for 1 h, then cooled to room temperature and reduced to dryness in vacuo to give diethyl ({[3-(3,5-dimethyl-4-isoxazolyl)-4-(methyloxy)phenyl]amino}methylidene)propanedioate (50.1 g), which after standing overnight became as a brown crystalline solid.

Workup

  1. temperatureThe solution was heated for 1 h
  2. temperaturecooled to room temperature

Sources & evidence

ORD record
ord-8192f2e887514843a7750a80f6099516
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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