Acetic Acid → ethyl (6E)-6-[(4-bromophenyl)hydrazinylidene]-6-phenylhexanoate

HRID 395587Notes

Reaction equation

Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.C([O-])(=O)C.[Na+].C(O)(=O)C.O=[C:21]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>O>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]/[N:10]=[C:21](/[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)\[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1.91 g (8.55.10−3 mol) of 4-bromophenylhydrazine hydrochloride and 0.73 g (8.9.10−3 mol) of sodium acetate in 17 ml of water is prepared and 2.05 ml (35.8.10−3 mol) of acetic acid are added. This mixture is subsequently heated to 70° C., with stirring, and a suspension of 2.0 g (8.54.10−3 mol) of ethyl ε-oxobenzenehexanoate in 27 ml of water is then added slowly. The reaction mixture is stirred at 70-80° C. for 45 min and then at room temperature for 12 hours, after which it is extracted with 2 times 50 ml of ethyl acetate. The organic phase is washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give 3.38 g of the expected compound, which is used directly in the next step.

Workup

customis prepared
additionis then added slowly
stirringThe reaction mixture is stirred at 70-80° C. for 45 min
extractionafter which it is extracted with 2 times 50 ml of ethyl acetate
washThe organic phase is washed with water
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c4b25c39ebd44f3e865c7db8db138490
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06605633B1

Reaction notes

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