Ethanol → HCID 67122874, compound

HRID 2046393Notes

Reaction equation

[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([NH2:9])[N:6]=[N:7][CH:8]=1.C(=O)(O)[O-].[Na+].[CH2:17](O)[CH3:18]>O>[F:11][C:2]([F:1])([F:10])[C:3]1[CH:8]=[N:7][N:6]2[CH:17]=[CH:18][N:9]=[C:5]2[CH:4]=1

Participants

Conditions

Temperature: 130 °C

Procedure

5-(Trifluoromethyl)pyridazin-3-amine (6.79 g, 41.6 mmol) was dissolved in a mixture of ethanol (133 mL) and water (33.3 mL) and 50% aq. solution of chloroacetylaldehyde (26.9 mL, 208 mmol) and sodium bicarbonate (17.5 g, 208 mmol) was added. The reaction was sealed in a pressure vessel and heated to 130° C. for 6 h. The reaction was then cooled to room temperature. Water was added and the mixture filtered through celite. The aqueous layer was extracted with a 3:1 mixture of CHCl3:Isopropanol (×3). The organic layers were collected, dried with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography to afford the title compound as an orange solid. 1H NMR (500 MHz, CDCl3) δ 8.52 (s, 1H); 8.27 (s, 1H); 8.13 (s, 1H); 7.97 (s, 1H). LRMS (APCI) calc'd for (C7H4F3N3) [M+H]+, 187.1. found 187.1.

Workup

additionwas added
customThe reaction was sealed in a pressure vessel
temperatureThe reaction was then cooled to room temperature
filtrationthe mixture filtered through celite
extractionThe aqueous layer was extracted with a 3:1 mixture of CHCl3
customThe organic layers were collected
dry with materialdried with magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-48641c739db543c681fd0c2e684d696b
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592425B2

Reaction notes

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