Hydrazine → (E)-1-(3-bromophenyl)-N-[(E)-(3-bromophenyl)methylideneamino]methanimine

HRID 2075351Notes

Reaction equation

[OH-].[Na+].[S].[NH2:4][NH2:5].[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=O>>[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)/[CH:10]=[N:4]/[N:5]=[CH:10]/[C:9]1[CH:12]=[CH:13][CH:14]=[C:7]([Br:6])[CH:8]=1

Participants

Reactant 4

HCID 9321Hydrazine

HCID 14798Sodium Hydroxide

HCID 765833-Bromobenzaldehyde

HCID 5362487Sulfur

Product 1

HCID 12755061(E)-1-(3-bromophenyl)-N-[(E)-(3-bromophenyl)methylideneamino]methanimineYield 80.6%

Conditions

Temperature: 85 °C

Procedure

To a 250 mL 3-neck round-bottom flask equipped with condenser was added sodium hydroxide (6.2 g, 156 mmol), sulfur (5.0 g, 156 mmol), and hydrazine (5.0 g, 156 mmol). The mixture was stirred at reflux 85° C. for 2 hours. The solution was cooled to room temperature and treated dropwise via syringe with 3-bromobenzaldehyde (18 mL, 156 mmol). The precipitate was recovered by filtration, washed with water and dried in an oven to provide (1E,2E)-1,2-bis(3-bromobenzylidene)hydrazine (23 g, 40%). LCMS (M+H) 367.1 calc. for C14H, Br2N2 366.9. 1H NMR (400 MHz, CDCl3): δ ppm 7.30-7.35 (m, 2H) 7.59 (d, J=7.82 Hz, 2H) 7.70-7.73 (d, 2H) 8.03 (s, 2H) 8.56 (s, 2H).

Workup

customTo a 250 mL 3-neck round-bottom flask equipped with condenser
temperatureThe solution was cooled to room temperature
filtrationThe precipitate was recovered by filtration
washwashed with water
customdried in an oven

Sources & evidence

ORD record: ord-b972dcdf154742a3be6fad711c940551
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919504B2

Reaction notes

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