Acetic Acid → 1-[(E)-(4-bromophenyl)methylideneamino]-1-methylurea

HRID 1772605Notes

Reaction equation

[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[NH2:10][N:11]([CH3:15])[C:12]([NH2:14])=[O:13].CC(O)=O.O>CCO.CCOCC>[Br:1][C:2]1[CH:9]=[CH:8][C:5](/[CH:6]=[N:10]/[N:11]([CH3:15])[C:12]([NH2:14])=[O:13])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-bromobenzaldehyde (4.30 g, 23.2 mmol) in EtOH (40 mL) was added 1-amino-1-methylurea (2.50 g, 28.1 mmol), AcOH (2.5 mL) and H2O (4.5 mL). The resulting solution was stirred at 80° C. overnight. After cooling to rt, Et2O (200 mL) was added. The resulting solids were collected by filtration to obtain compound 10a as a white solid (5.80 g, 97% yield). Mass Spectrum (LCMS, ESI pos.): Calcd. for C9H10BrN3O: 256.0 (M+H). Found 256.1.

Workup

temperatureAfter cooling to rt
filtrationThe resulting solids were collected by filtration

Sources & evidence

ORD record: ord-15f8ab8311d0499eac52e35711296984
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249163B2

Reaction notes

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