2-Chlorophenylhydrazine hydrochloride → HCID 118432122, compound

HRID 2207946Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[C:4](=O)[CH:5]=[CH:6][C:7]1[S:8][C:9]([Br:12])=[CH:10][CH:11]=1.Cl.[Cl:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][NH2:24]>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH2:5][CH:6]([C:7]2[S:8][C:9]([Br:12])=[CH:10][CH:11]=2)[N:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[Cl:16])[N:24]=1)=[O:14]

Participants

Conditions

Temperature: 125 °C

Procedure

4-(5-Bromo-thiophen-2-yl)-2-oxo-3-butenoic acid methyl ester (19.9 mg, 72.2 mmol) prepared in Step 2 and 2-chlorophenylhydrazine hydrochloride (14.2 g, 79.4 mmol) were added to acetic acid (250.0 mL). The reaction mixture was stirred at 125° C. for 3 hours, concentrated under reduced pressure, and then ethyl acetate was added thereto. The reaction 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: ethyl acetate/n-hexane=1/6) to give 18.9 g of the titled compound as a pale yellow liquid.

Workup

concentrationconcentrated under reduced pressure
additionethyl acetate was added
washThe reaction 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: ethyl acetate/n-hexane=1/6)

Sources & evidence

ORD record: ord-1937716874d5405e848de58b0cc2db0d
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376420B2

Reaction notes

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