Diphenyl Ether → HCID 10448324, compound

HRID 1486935Notes

Reaction equation

HRID 1486935 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]=[C:10]([C:16]([O:18]CC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:4][C:3]=1[F:21].C1(OC2C=CC=CC=2)C=CC=CC=1>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[F:21])[NH:8][CH:9]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:16]2=[O:18]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 86628010HCID 86628010, compound

Product 1

HCID 10448324HCID 10448324, compoundYield 64%

Conditions

Temperature
70 °C

Procedure

A solution of diethyl 2-[[(4-bromo-3-fluorophenyl)amino]methylidene]propanedioate (90 g, 249.88 mmol) in diphenyl ether (600 mL, 3.79 mol) was stirred at 240° C. for 2.5 h. The mixture was allowed to cool to 70° C., the solids collected by filtration and dried in a vacuum oven to afford the desired material (50 g, 64%) as a white solid which was used without further purification. NMR Spectrum: 1H NMR (500 MHz, DMSO-d6, (100° C.)) δ 1.26-1.33 (3H, m), 4.25 (2H, q), 7.52 (1H, d), 8.37 (1H, d), 8.48 (1H, s), 12.05 (1H, s). Mass Spectrum: m/z (ES+)[M+H]+=314.

Workup

  1. filtrationthe solids collected by filtration
  2. customdried in a vacuum oven

Sources & evidence

ORD record
ord-af9314c019bb42069e7f43a3ea4f7325
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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