Benzoyl chloride → N'-benzoyl-4-bromobenzohydrazide

HRID 2076734Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.CN1CCCC1=O.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[C:19]([NH:9][NH:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a 200 mL three-necked flask were placed 15 g (71 mmol) of 4-bromobenzoylhydrazine and 20 mL of N-methyl-2-pyrrolidone (abbreviation: NMP). To this mixture was dripped a solution of 9.4 mL (81 mmol) of benzoyl chloride in 5 mL solution of N-methyl-2-pyrrolidone through a 50 mL dropping funnel. This solution was stirred at 80° C. for 3 hours under a stream of nitrogen. After a predetermined time, this solution was added to about 100 mL of water, and the precipitated solid was collected by suction filtration. The collected solid was washed with methanol, and 19 g of a white powder, which was a target substance, was obtained at a yield of 84%.

Workup

customIn a 200 mL three-necked flask were placed
filtrationthe precipitated solid was collected by suction filtration
washThe collected solid was washed with methanol, and 19 g of a white powder, which
customwas obtained at a yield of 84%

Sources & evidence

ORD record: ord-d983f28795d04a6ea9460862e3a49a02
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07927720B2

Reaction notes

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