2-Chlorophenylhydrazine hydrochloride → HCID 118431639, compound

HRID 2207877Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10](=O)[C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH:5]=[CH:6][CH:7]=1.Cl.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH:27][NH2:28]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]2[N:27]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[Cl:20])[N:28]=[C:10]([C:11]([F:17])([F:16])[C:12]([F:15])([F:14])[F:13])[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1-(3-Bromo-phenyl)-4,4,5,5,5-pentafluoro-pent-1-en-3-one (1.4 g, 4.3 mmol) prepared in Step 1 of Preparation 5 and 2-chlorophenylhydrazine hydrochloride (0.8 g, 4.3 mmol) were added to acetic acid (30.0 mL). The reaction mixture was stirred at 100° C. for 12 hours, concentrated under reduced pressure, and then ethyl acetate was added thereto. The mixture was washed with a saturated solution of sodium hydrogen carbonate, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: diethyl ether/n-hexane=1/9) to give 1.1 g of the titled compound as a brown liquid.

Workup

concentrationconcentrated under reduced pressure
additionethyl acetate was added
washThe mixture was washed with a saturated solution of sodium hydrogen carbonate
dry with materialdried on anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customto give a yellow liquid residue
customThe resulting residue was purified by silica gel column chromatography (eluent: diethyl ether/n-hexane=1/9)

Sources & evidence

ORD record: ord-3c79d77ff7a74f5bb9ec987695e15ade
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376420B2

Reaction notes

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