4-Chloro-2-methoxy-6-methylaniline → 7-Bromo-N-(4-chloro-2-methoxy-6-methylphenyl)-1-methyl-1H-benzimidazol-2-amine

HRID 1698542Notes

Reaction equation

[Br:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9](=O)[NH:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:20]=[C:19]([CH3:21])[C:17]([NH2:18])=[C:16]([O:22][CH3:23])[CH:15]=1>CN1CCCC1=O.ClCCl>[Br:1][C:2]1[C:7]2[N:8]([CH3:12])[C:9]([NH:18][C:17]3[C:19]([CH3:21])=[CH:20][C:14]([Cl:13])=[CH:15][C:16]=3[O:22][CH3:23])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of 7-bromo-1-methyl-1,3-dihydro-2H-benzimidazol-2-one 2.32 g (9.69 mmol) and 4-chloro-2-methoxy-6-methylaniline 4.98 g (29.1 mmol) in 0.5 mL of N-methyl-2-pyrrolidone was heated at 110° C. for 2 days. The reaction was cooled to room temperature and diluted with dichloromethane. The mixture was washed with sodium bicarbonate and water, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with ethyl acetate/hexane (1:1) to give 3.13 g (8.23 mmol, 85%) of the title compound.

Workup

temperatureThe reaction was cooled to room temperature
washThe mixture was washed with sodium bicarbonate and water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was triturated with ethyl acetate/hexane (1:1)

Sources & evidence

ORD record: ord-36d63c97986b4ce3bc5c281d2e673b11
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163935B2

Reaction notes

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