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

HRID 718644Notes

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 (4.3 g, 23 mmol) and 1-amino-1-methylurea (2.5 g, 28 mmol) in EtOH (40 mL) was added AcOH (2.5 mL) and water (4.5 mL). The resulting solution was stirred overnight at 80° C. and allowed to cool to rt. A precipitate formed by the addition of Et2O (50 mL). The solids were collected by filtration and compound 51a was obtained as a white solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C9H10BrN3O: 256.0 (M+H). Found 256.1.

Workup

temperatureto cool to rt
filtrationThe solids were collected by filtration

Sources & evidence

ORD record: ord-362d1fac14ff47369da0d3dcde69de63
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193736B2

Reaction notes

Loading…