Sulfuric Acid → HCID 86620836, compound

HRID 736286Notes

Reaction equation

Cl.[Br:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[C:11]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.S(=O)(=O)(O)O>C(O)C>[C:11](=[N:10][NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([Br:2])[CH:4]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

(3-Bromophenyl)hydrazine hydrochloride (10 g, 44 mmol, 1 eq.), benzophenone (8.14 g, 44 mmol, 1 eq.) and ethanol (100 mL) are placed in a 250 mL round-bottomed flask. 2 mL of concentrated sulfuric acid are then added. The resulting suspension is heated at a temperature in the region of 80° C. After 30 minutes at this temperature, the suspension becomes a solution. The solution is stirred at this temperature for 18 hours, and is then concentrated to 95%. The residue is diluted with ethyl acetate and washed with sodium hydrogen carbonate solution. After drying over magnesium sulfate, the solution is concentrated and the residue is purified by chromatography on a column of silica gel, eluting with an ether/heptane mixture (3/97 by volume). 15 g (95%) of N-benzhydrylidene-N′-(3-bromophenyl)hydrazine are thus obtained.

Workup

concentrationis then concentrated to 95%
additionThe residue is diluted with ethyl acetate
washwashed with sodium hydrogen carbonate solution
dry with materialAfter drying over magnesium sulfate
concentrationthe solution is concentrated
customthe residue is purified by chromatography on a column of silica gel
washeluting with an ether/heptane mixture (3/97 by volume)

Sources & evidence

ORD record: ord-4837983e3ee9403d9fcb8d2f61122bb4
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595320B2

Reaction notes

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