Formamide--water (1/1) → 3-Methyl-1-phenyl-5-(5-m-tolyl-1H-imidazol-4-yl)-1,3-dihydro-benzoimidazol-2-one

HRID 1828169Notes

Reaction equation

Br[CH:2]([C:22]1[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=1)[C:3]([C:5]1[CH:21]=[CH:20][C:8]2[N:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10](=[O:13])[N:11]([CH3:12])[C:7]=2[CH:6]=1)=O.CON(C)C(C1C=CC2[N:38](C3C=CC=CC=3)[C:39](=O)[NH:40]C=2C=1)=O.O.C(N)=O>[OH-].[NH4+]>[CH3:12][N:11]1[C:7]2[CH:6]=[C:5]([C:3]3[N:38]=[CH:39][NH:40][C:2]=3[C:22]3[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=3)[CH:21]=[CH:20][C:8]=2[N:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]1=[O:13]

Participants

Conditions

Temperature: 140 °C

Procedure

5-(Bromo-m-tolyl-acetyl)-3-methyl-1-phenyl-1,3-dihydro-benzoimidazol-2-one (prepared from 2-oxo-1-phenyl-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methoxy-methyl-amide as described in the general procedure, 0.26 gm, 0.60 mmol) was added to 5 mL of 8% water/formamide and the mixture was heated to 140° C. for 14 hours. The reaction mixture was then cooled to room temperature and diluted with 20 mL of ammonium hydroxide with rapid stirring. After stirring for ½ hour, the solid precipitate was filtered and purified by column chromatography (0.5% methanol in ethyl acetate) to afford 75 mg of the title compound. MS (M+1)=381.2

Workup

temperatureThe reaction mixture was then cooled to room temperature
filtrationthe solid precipitate was filtered
custompurified by column chromatography (0.5% methanol in ethyl acetate)

Sources & evidence

ORD record: ord-1ad5c39038824b989faa9d217f22beb1
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056918B2

Reaction notes

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