Ethyl 3-[(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylate → HCID 57617105, compound

HRID 1879271Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][C:11]([O:13]CC)=O)=[CH:4][C:3]=1[O:22][CH3:23]>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:22][CH3:23])[NH:8][C:9]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH:10][C:11]2=[O:13]

Participants

Conditions

Temperature: 300 °C

Procedure

DOWTHERM A (0.19 M) was heated to reflux (˜300° C.). A mixture of the product 113 in DOWTHERM A (2.5 M) was added to the heated DOWTHERM A solution portionwise. The mixture was stirred at reflux for 1 h after the addition was complete. The mixture was cooled to RT, filtered, and the solid was washed with hexane to give the title compound 114 (86%). 1H NMR (DMSO-d6) (ppm) 11.69 (s, 1H), 8.19 (s, 1H), 7.82 (m, 2H), 7.59 (m, 3H), 7.35 (s, 1H), 6.33 (s, 1H), 3.96 (s, 3H).

Workup

temperatureat reflux for 1 h
additionafter the addition
temperatureThe mixture was cooled to RT
filtrationfiltered
washthe solid was washed with hexane

Sources & evidence

ORD record: ord-591e420a93e4465f9399c4b121b16460
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314062B2

Reaction notes

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